Month: July 2021

Application of 19094-56-5,Some common heterocyclic compound, 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, molecular formula is C7H4ClIO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation of 2-Chloro-5-Iodobenzoyl Chloride A 1 L 4-necked flask equipped with thermometer and mechanical stirrer (operating at 150 RPM) was charged with 2-chloro-5-iodobenzoic acid (14.1 g, 0.05 mol), DCM (70.5 mL) and oxalyl chloride (5.5 mL, 0.06 mol). After stirring for 10 min, the mixture was cooled to 10 to 15 C. and DMF (0.15 mL, 1.92 mmol) was added by syringe over 10 min in two bolus of 0.1 and 0.05 mL while keeping the reaction temperature below 20 C. After the addition was completed, the mixture was warmed to 25 C. and stirred for 16 h. The mixture was concentrated and the residue was dried under vacuum at 30 C. for 5 h to give 15.0 g of product as a white solid. Yield: 100%. LCMS-0013: 99% Purity. 1H NMR (CDCl3, 400 MHz): 8.33 (d, J=2.4 Hz, 1H), 7.81?7.84 (dd, J=2.4 Hz, 8.4 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H).

The synthetic route of 19094-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Theracos, Inc.; Xu, Baihua; Lv, Binhua; Xu, Ge; Seed, Brian; Roberge, Jacques Y.; US2013/267694; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 54413-93-3,Some common heterocyclic compound, 54413-93-3, name is 2-Iodo-5-methoxybenzoic acid, molecular formula is C8H7IO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of 2-bromo-6-methoxybenzoic acid (104 mg, 397 mumol) in CH2Cl2 (3.0 mL) were added chloromethlenedimethyliminium chloride (50.8 mg, 397 mumol) at 0 °C under Ar atmosphere, then the mixture was stirred at room temperature for 1 h. At 0 °C, 2-(4-butylaminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (29g)24 (50.0 mg, 159 mumol) and Et3N (166 mul, 1.19 mmol) then the mixture was stirred for 3 h, and was allowed to warm to room temperature. At 0 °C, the mixture was diluted with ethyl acetate and then water was added. The organic layer was separated and washed with brine, and dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography (n-hexane/AcOEt = 1:0-1:1) to give 30g (73.5 mg, 139 mumol, 88percent) as a colorless oil.

The synthetic route of 54413-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aoyama, Hiroshi; Sugita, Kazuyuki; Nakamura, Masahiko; Aoyama, Atsushi; Salim, Mohammed T.A.; Okamoto, Mika; Baba, Masanori; Hashimoto, Yuichi; Bioorganic and Medicinal Chemistry; vol. 19; 8; (2011); p. 2675 – 2687;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 21740-00-1,Some common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, molecular formula is C7H4BrIO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

5-Bromo-2-iodobenzoic acid (409 mg, 1.25 mmol), /V-(3-dimethylaminopropyl)-A^- ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol), 1-hydroxybenzotriazoe (135 mg, 1.0 mmol), 7V,/V-diisopropylethylamine (523 pL, 3.0 mmol), and benzyl amine (109 pL, 1.0 mmol) were dissolved in anhydrous DMF (5 mL) and stirred at room temperature for 16 hr. The reaction mixture was diluted with an excess of EtOAc and washed five times with water and brine. The organic layer was dried over Na?.S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : DCM ::: 0 : 100 to 30 : 70) to give JV-benzyl- 5-bromo-2-iodobenzamide (361 mg, 87 %) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-iodobenzoic acid, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164948; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 108078-14-4, name is 2-Iodo-3-methylbenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 108078-14-4

BEAD LOADING Rink Amide MBHA resin (87 mg, 0.06 mmol, 0.69 mmol/g loading) was pre-swelled in a 5 mL disposable syringe equipped with a frit by rotating with DCM (3 mL) for 1 h. The resin was then washed with DMF (5 X 4 mL). The Fmoc protecting group on the bead was removed by treatment with 5 bed volumes (ca. 4 mL) of a 20% piperidine solution in DMF for 20 min. Meanwhile, Fmoc-Phe-OH (116 mg, 0.3 mmol, 5 equiv) was dissolved in DMF (3 mL) along with HOBt (41 mg, 0.3 mmol, 5 equiv). Diisopropyl carbodiimide (DIC) (50 muL, 0.3 mmol, 5 equiv) was then added and the resulting mixture was stirred at room temperature for 20 min. After 20 minutes, the resin was washed with DMF (5 X 4 mL). To the thoroughly washed resin bed, was added the coupling solution (Fmoc-Phe-OH,HOBt, and DIC), and the resulting mixture was rotated for 12 h. The loaded resin was then washed with DMF (5 X 4 mL) and used in subsequent Fmoc solid phase peptide synthesis as described below. FMOC REMOVAL The Fmoc group of the terminal amino acid of the growing peptide chain was deprotected by treating the resin beads (0.69 mmol/g loading) with a 20% solution of piperidine in DMF (ca. 4 mL) with rotation for three minutes. The deprotection cocktail was then discharged from the syringe and the resin beads were treated with a fresh portion of 20% piperidine in DMF for three minutes.This protocol is repeated until the resin beads have been treated with four aliquots of 20% piperidine in DMF. The final portion is then discharged from the syringe and the deprotected beads are washed with DMF (5 X 4 mL). The washed, deprotected resin beads were then immediately coupled with the next amino acid in the sequence. HOBT-MEDIATED COUPLING The next amino acid in a desired sequence was activated as the HOBt ester by dissolving the desired amino acid (0.3 mmol, 5 equivalents relative to the 0.69 mmol/g resin loading) along with HOBt (41 mg, 0.3 mmol, 5 equiv) in DMF/DCM (1:1) (3 mL). To the resulting solution was added DIC (50 muL, 0.3mmol, 5 equiv) and the resulting solution was stirred at room temperature for twenty minutes (usually while the terminal amino acid of the resin bound sequence is deprotected).The resulting solution of HOBt ester was added to the N-terminal deprotected, resin-bound, peptide sequence and the mixture was rotated for one hour. The resin beads were then thoroughly washed with DMF (5 X 4 mL). The resulting N-terminal, Fmoc-protected, resin-bound peptide sequence was then resubjected to the Fmoc removal protocol and subsequent HOBt couplings until the desired sequence had been assembled. N-TERMINAL O-IODOBENZOATE CAPPING The N-terminus of the peptide was capped with the o-iodoarylamido active site by the HOBt active ester methodology. The o-iodobenzoic acid (0.3 mmol, 5 equivalents relative to the 0.69 mmol/g resin loading) was dissolved along with HOBt (41 mg, 0.3 mmol, 5 equiv) in DMF/DCM (1:1) (3 mL). To the resulting solution was added DIC (50 muL, 0.3 mmol, 5 equiv) and the resulting solution was stirred at room temperature for twenty minutes (usually while the terminal aminoacid of the resin bound sequence is deprotected).The resulting solution of HOBt ester was added to the N-terminal deprotected, resin-bound, peptide sequence and the mixture was rotated for one hour. The resin beads were then thoroughly washed with DMF (5 X 4 mL). TFA CLEAVAGE/GLOBAL SIDE-CHAIN DEPROTECTION OF PEPTIDES Peptides were cleaved from the resin beads by employing the following protocol: The fully assembled, resin-bound peptides were prepared for cleavage by washing the beads with DMF (5 X 4 mL), DCM (5 X 4 mL), and methanol (5 X 4mL). The syringe plunger was removed from the barrel and the resin beads were dried overnight in the vacuum oven at 25 C. The following day, the resin was treated with a cleavage cocktail comprised of a mixture of TFA/H2O/TIS(95:2.5:2.5) (3 mL) for 2.5 h with minimal, intermittent agitation. The cleavage cocktail, containing the solvated, resin-free peptide was then ejected into a 5 mL pear-shaped flask and the solvent was removed under a stream of nitrogen to give a thick oil. The crude peptide was then precipitated by the addition of ice-cold diethyl ether. The solid peptide was then isolated by vacuum filtration and washed with copious amounts (ca. 15-20 mL) of cold ethyl ether. The solid peptide was then dried in vacuo. The identity of the desired sequence was verified by MALDI-TOF mass spectrometry.

According to the analysis of related databases, 108078-14-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Whitehead, Daniel C.; Fhaner, Matthew; Borhan, Babak; Tetrahedron Letters; vol. 52; 18; (2011); p. 2288 – 2291;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 202865-85-8, name is 1-Bromo-4-iodo-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 202865-85-8

Compound K45 can be synthesized by a person of ordinary skill following Scheme 25 illustrated in FIG. 26. In the first step, compound S25-1 (available for purchase from ArkPharm, Inc., CAS No. 57103-02-3) is combined with BOC anhydride and DMAP in THF. The mixture is taken, without purification and combined with HNPh2, tBu3P, and Pd2dba3 in toluene. This mixture is taken, without purification and combined with TFA to produce compound S25-2. In the second step, compound S25-2 is combined with compound S25-3 (available for purchase from Alfa Aesar, CAS No. 202865-85-8), K3P04 and Cul in toluene at 80 C and stirred for 6 hours to form compound S25-4. In the third step, compound S25-4 is cooled to -78 C in hexanes solution before dropwise addition of nBuLi and subsequent dropwise addition of Bu3SnCl to form compound S25-5. In the fourth step, compound 25-5 is combined with compound S25-6 (available for purchase from Acros Organics, CAS No. 106-37-6) and Pd(OAc)2 in THF at 45 C and stirred for 24 hours to give compound S25-6. In the fifth step, compound S25-6 is cooled to -78 C in hexanes solution before dropwise addition of nBuLi and subsequent dropwise addition of Bu3SnCl to form compound S25-7. In the sixth step, compound S25-7 is combined with compouns S25-8 (available for purchase from eNovation Chemicals, CAS No. 40000-20-2) and Pd(OAc)2 in THF at 45 C and stirred for 24 hours to give compound K45. It is understood that steps 1, 2, 3, 4, 5, and 6 can be performed and optimized by a person having ordinary skill in the art without undue experimentation.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 202865-85-8.

Reference:
Patent; Harvard College Dean Deng; A ·asipulu-gujike; R ·gemaisi-bomubaleierli; T ·D·xiseer; J ·akuileila-aipalakuilei; R ·P·yadangsi; D ·maikelaolin; D ·K·duweinade; (333 pag.)CN106661001; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 112671-42-8, SDS of cas: 112671-42-8

Under the protection of argon, dibenzothiophene-4-boronic acid (29.2 g, 128.1 mmol), 4-bromo-1-iodo-2-nitrobenzene (35.0 g, 106.8 mmol), Na2CO3 were sequentially added to the reaction flask. (34.0 g, 320.4 mmol), tetrakistriphenylphosphine palladium (6.17 g, 5.3 mmol), toluene (640 ml) and ethanol (160 ml), and the reaction mixture was stirred at 90 C for 3 hours. After the stirring was completed, poured into distilled water (160 ml), cooled to room temperature, and the organic phase was extracted with ethyl acetate.The organic phase is concentrated and combined by column chromatographyC5 (33.6 g, 82%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Zhou Wenting; Cai Hui; (39 pag.)CN108822020; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 355-43-1, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 355-43-1, Formula: C6F13I

A 100 ml Schlenk flask equipped with a stir bar was flame-dried and then charged with 1,4-diiodobenzene (3.30 g, 10 mmol), Cu powder (5.08 g, 80 mmol), and 2,2′-bipy (156 mg, 1 mmol). The flask was evacuated and back-filled with argon three times. Anhydrous dimethylsulfoxide (30 mL) was added via a syringe. Perfluorohexyl iodide (6.5 mL, 30 mmol) was added dropwise while stirring. Upon completion of addition, the reaction mixture was heated to 70 C. for 72 hours then removed from heat. The reaction mixture was poured into 100 mL H2O/100 mL diethyl ether and stirred vigorously for 30 min. Solid residues were removed by filtration, and the organic layer was washed twice with dilute NH4OH solution, twice with water, dried over MgSO4. The solvent was removed by evaporation under reduced pressure, and the resulting off-white solids were subjected to sublimation to give S5 as white solids (5.61 g, 78%). 1H NMR (300 MHz, CDCl3): delta 7.77 (s, 4H). 19F NMR (282 MHz, CDCl3): delta -126.58 (4F), -123.26 (4F), -122.15 (4F), -121.87 (4F), -111.71 (4F), -81.16 (6F).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Massachusetts Institute of Technology; Swager, Timothy M.; Lim, Jeewoo; Takeda, Yohei; US9156938; (2015); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H4F3I

General procedure: To a resealable Schlenk tube were added indole (1.0 mmol), K3PO4 (0.424 g, 2.0 mmol), and MCM-41-2N-CuI (88 mg, 0.04 mmol), and the reaction vessel was fitted with a rubber septum. The vessel was evacuated and back-filled with argon and this evacuation/back-fill procedure was repeated one additional time. The aryl halide (1.2 mmol) and toluene (2 mL) were then added under a stream of argon. The reaction tube was quickly sealed and the contents were stirred while heating in an oil bath at 110 C for 24-48 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (5 mL), and filtered. The MCM-41-2N-CuI complex was washed with distilled water (2×5 mL), ethanol (2×5 mL), and Et2O (2×5 mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (petroleum/ethyl acetate=50:1 to 4:1) to provide the desired product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 401-81-0.

Reference:
Article; Xiao, Ruian; Zhao, Hong; Cai, Mingzhong; Tetrahedron; vol. 69; 26; (2013); p. 5444 – 5450;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

39998-81-7, name is 2-Fluoro-4-iodo-1-methylbenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 39998-81-7

Methyl-2-fluoro-4-iodo benzoate (Reagent G) A solution of 2-fluoro-4-iodo toluene (5 g, 26.6 mmol) in pyridine (2 mL) and water (20 mL) was treated with potassium permanganate (16.6 g, 105 mmol) and heated at 150 C. overnight. The reaction mixture was then cooled to room temperature and filtered and the filtrate was extracted with hexane. The aqueous phase was acidified with 10% hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was dissolved in 20 mL of methanol, treated with concentrated sulfuric acid (1 mL) and refluxed overnight. The volatiles were distilled off in vacuo and the residue was dissolved in diethyl ether, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent afforded the title compound as an oil (0.26 g, 5%). 1H NMR (300 MHz, CDCl3):delta 7.60 (m, 4H), 3.93 (s, 3H).

The synthetic route of 39998-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan Sales, Inc.; US6252090; (2001); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 25252-00-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 25252-00-0 as follows.

Part C. 3′-(1-benzyl-6-cyano-1H-indol-3-ylmethyl)-4-carbamoyl-biphenyl-2-carboxylic acid benzyl ester:; 2-Bromo-5-iodobenzoic acid (6.54 g, 20.0 mmol) was dissolved in DMF (70 mL). Potassium bicarbonate (2.2 g, 22.0 mmol) was added, followed by benzyl bromide (2.8 mL, 22.0 mmol). The mixture was stirred at rt under N2 for 12 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organic solution was washed with brine, dried over MgSO4, and concentrated and dried to give 9.05 g of the benzyl ester. The ester (2.3 g, 7.69 mmol), Zn(CN)2 (1.3 g, 11.5 mmol), and Pd[PPh3]4 were dissolved together in 25 mL of DMF. The mixture was de-gassed and heated at 90 C. for 4 h. Reaction mixture was concentrated and purified by chromatography (silica gel, 5% EtOAc in hexane) to give 1.8 g of the benzonitrile. MS: 316.0, 317.9 (M+1)+. The benzonitrile (1.4 g, 4.4 mmol) was dissolved in 15 mL of DMF. The reaction mixture was cooled at 0 C. Potassium carbonate (0.20 g, 1.45 mmol) was added, followed by dropwise addition of 30% hydrogen peroxide solution (1.2 mL). The cooling bath was removed and the mixture was stirred at rt for 12 h. The reaction was quenched with aqueous NaHSO3 and water. The formed precipitate was filtered and dried to give 1.1 g of the desired amide. MS: 334.2, 336.3 (M+1)+. A mixture of the resulting amide (0.2 g, 0.6 mmole), bis(pinacolato)diboron (0.228 g, 0.9 mmol) and anhydrous KOAc (0.18 g, 1.8 mmol) in 2 mL of 1,4-dioxane was purged with argon, then (1,1′)-bis(diphenylphosphino)ferrocene)palladium(II) chloride (20 mg, 0.024 mmol) was added. The resulting mixture was heated in a sealed tube in a microwave reactor at 100 C. for 2 h then left standing overnight at rt. The reaction was diluted with water and extracted 3× with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the boronate (0.13 g, 57%). A mixture of this compound, the compound of Part B (0.1 g, 0.25 mmol), and K3PO4 (0.11 g, 0.5 mmol) in 5 mL dioxane was degassed and then treated with tetrakis(triphenylphosphine)palladium(20 mg, 0.017 mmol). The resulting mixture was heated in a 95-100 C. oil bath under N2 for 2 h, then stirred at rt overnight. The reaction mixture was diluted with brine and extracted 3× with EtOAc. The combined extracts were washed with brine then dried over anhydrous Na2CO3, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the product (0.12 g, 83%) as a light yellow foam. 1H NMR (400 MHz, CDCl3) delta ppm 4.07 (s, 2H) 4.90 (s, 2H) 5.23 (s, 2H) 6.91 (d, J=6.15 Hz, 2H) 7.05 (m, 3H) 7.20 (m, 6H) 7.29 (m, 5H) 7.42 (d, J=7.91 Hz, 1H) 7.51 (d, J=10.99 Hz, 2H) 7.98 (dd, J=8.13, 1.98 Hz, 1H) 8.19 (d, J=2.20 Hz, 1H). LC/MS m/z 576.16 (M+H)+.

According to the analysis of related databases, 25252-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com