Tag: M.W=300-400

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 199786-58-8, name is (5-Bromo-2-iodophenyl)methanol, A new synthetic method of this compound is introduced below., Quality Control of (5-Bromo-2-iodophenyl)methanol

A solution of 9.59 mmol (5-bromo-2-iodo-phenyl)-methanol [199786-58-8] in 10 ml of N,N-dimethylformamide is added at room temperature dropwise to a mixture of 11.5 mmol of sodium hydride (60% in paraffine) in 20 ml of N,N-dimethylformamide. The mixture is stirred for 1 h at room temperature. 10.6 mmol of tert-butyl-dimethyl- chloro silane and 1.00 mmol of potassium iodide are added and the mixture stirred for 30 minutes at room temperature. The reaction is quenched with water and extracted with toluene. The combined organics are washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. , The resulting residue is purified by flash chromatography (SiO2 60F) to afford the title compound as colourless oil. Rf = 0.35 (dichloromethane); Rt = 11.31 (gradient II).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SPEEDEL EXPERIMENTA AG; WO2008/119744; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

17024-12-3, name is 9-Iodophenanthrene, 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. Recommanded Product: 17024-12-3

Synthesis of 1-[5-(1 ,1 ,3,3-tetramethylisoindolin-2-yloxylyl)-2-[9-(phenanthryl)]acetylene; 205 2079-lodophenanthrene (59 mg, 0.194 mmol), DABCO (62.5 mg, 0.557 mmol, 3 equiv) and Pd(OAc)2 (1 mg, 2.5 mol %) was dissolved in dry MeCN (1 cm3). 5-ethynyl- 1,1,3,3-tetramethylisoindolin-2-yloxyl 205 (50 mg, 0.233 mmol, 1.2 equiv) was added and mixture heated at 80 0C under argon for 4 h. Subsequently the solvent was removed under reduced pressure and the residue taken up in CHCI3 (~1 ml) ensuring the DABCO remained undissolved. Purification of the resulting solution by column chromatography (SiO2, eluant:10 % EtOAc, 90 % n-Hexane) gave 1 -[5-(1 , 1,3,3- tetramethylisoindolin-2-yloxylyl)-2-[9-(phenanthryl)]acetylene, 207 (68 mg, 0.175 mmol, 90 %).

The synthetic route of 17024-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; QUEENSLAND UNIVERSITY OF TECHNOLOGY; WO2007/124543; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 629-09-4, A common heterocyclic compound, 629-09-4, name is 1,6-Diiodohexane, molecular formula is C6H12I2, its 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.

Step-1 : Synthesis of 2-(6-iodohexyl)isoindoline-l,3-dione (3377) [1175] To a suspension of potassium phthalamide (700 mg, 3.7 mmol) in DMF (30 mL) was added 1 ,6-diiodohexane (3.83 g, 11.33 mmol) and the reaction mass was heated atw 80 C for 1 h. (The reaction mass became clear on heating). The reaction mixture was cooled to RT, diluted with diethyl ether (100 mL) and water (100 mL), the organic layers were separated, and the aqueous layer was again extracted with diethyl ether (2×100 mL). The combined organic layer was washed with water (200 mL) and saturated brine solution (200 mL) The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the product, which was purified by column (3378) chromatography (silica gel: 100-200 mesh; Eluent: 10 % ethyl acetate in hexane) to obtain pure product as white solid (2.1 g).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; HUNG, David; CHAKRAVARTY, Sarvajit; RAI, Roopa; BERNALES, Sebastian; SATHE, Balaji Dashrath; URETA, Gonzalo; MCCULLAGH, Emma; WO2015/116707; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 63131-30-6, The chemical industry reduces the impact on the environment during synthesis 63131-30-6, name is Ethyl 3-(4-iodophenyl)-3-oxopropanoate, I believe this compound will play a more active role in future production and life.

To a solution of compound 56A (31.5 g, 99.02 mmol) in EtOH (300 mL) was added NH4OAc (20 g, 259.46 mmol), then the mixture was stirred at 85 C for 18h. The reaction mixture was concentrated to remove solvent, then diluted with water (150 mL) and extracted with EA (100 mL x 3), the organic layers were washed with saturated NaHCCL (100 mL x 2), dried over Na2S04, filtered and concentrated to give a residue. The residue was purified by flash silica gel chromatography (ISCO; 220 g SepaFlash Silica Flash Column, Eluent of 0-10% Ethyl acetate/Petroleum ethergradient 100 mL/min). Compound 56B (26 g, yield: 71.5%) as light yellow solid was obtained. 1H NMR (400MHz, DMSO-d6) d 7.86 – 7.75 (m, 2H), 7.44 – 7.34 (m, 2H), 4.77 (s, 1H), 4.05 (q, / = 7.1 Hz, 2H), 1.19 (t, / = 7.2 Hz, 3H). MS (ESI) m/z (M+H)+3l7.9.

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, Ethyl 3-(4-iodophenyl)-3-oxopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLADE THERAPEUTICS, INC.; LIM, Sharlene; IBRAHIM, Prabha; FUENTES, Maria; (0 pag.)WO2020/6294; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 755027-18-0, These common heterocyclic compound, 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, its 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.

A mixture of pyrazole-4-amine dihydrochloride (0.75 g, 4.79 mmol), salicylaldoxime (0.13115 g, 0.96 mmol), cesium carbonate (4.69 g, 14.38 mmol), cuprous oxide (0.06 g, 0.29 mmol), 1-bromo-4-iodo-2-methoxybenzene (1.5 g, 4.79 mmol) and N, N-dimethyl-formamide (5 ml) werecombined in a microwave vial fitted with an N2 inlet and magnetic stir bar. The reaction mixture wasstirred under a nitrogen atmosphere at 90 oc overnight. The solution obtained was allowed to coolto RT, then filtered through celite and the filtrate was concentrated in vacuo. The crude material20 was purified by silica gel chromatography (10% to 60% EtOAc in heptanes) to give 1-(4-bromo-3-methoxyphenyl)-1 H-pyrazol-4-amine (250 mg, MS: 270.2 [M+H+].)

Statistics shows that 1-Bromo-4-iodo-2-methoxybenzene is playing an increasingly important role. we look forward to future research findings about 755027-18-0.

Reference:
Patent; NOVARTIS AG; CHEUNG, Atwood; CHIN, Donovan Noel; DALES, Natalie; FAZAL, Aleem; HURLEY, Timothy Brian; KERRIGAN, John; O’BRIEN, Gary; SHU, Lei; SUN, Robert; SUNG, Moo; WO2014/28459; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 629-09-4, A common heterocyclic compound, 629-09-4, name is 1,6-Diiodohexane, molecular formula is C6H12I2, its 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.

Example 42-Amino-4-(6-fluorohexyl)-pentane dioic acid a) (2S.4S)-2-tert-Butoxycarbonylamino-4-(6-iodohexyl)-pentane dioic acid dimethyl ester 5.51 g (20 mmol) of Boc-L-Glutamic acid dimethylester (Advanced Chemtech) were dissolved in 60 mL of tetrahydrofuran (THF) and cooled to -70 0C. 44 mL (44 mmol) of 1 M solution of lithium-bis(trimethylsilyl)amide in THF was added drop wise over a period of 1 hour at -70 0C and stirring was continued over 2 h at -70 0C. Then 20.28 g (60 mmol) of 1,6- diiodohexane were added drop wise and, after 2 h at -70 0C, the cooling bath was removed and 100 mL of 2 N hydrochloric acid and 300 mL of ethyl acetate were added. The organic phase was separated, washed neutral with water, dried over sodium sulphate, filtered and the filtrate was reduced in volume by evaporation. The resulting crude product was chromatographed with hexane / ethyl acetate on silica gel. The resulting fractions were combined and reduced in volume by evaporation. Yield: 0.2 g (2.1 %)MS (ESIpos): m/z = 486 [M+H]+1 H NMR (300 MHz, CHLOROFORM-c/) d ppm 1.20-1.70 (m, 29H) 1.75-2.10 (m, 5H) 2.40- 2.50 (m, 1 H) 3.14-3.20 (m, 2H), 3.50-3.75 (m, 3H), 4.15-4.25 (2H) 4.32-4.42 (m, 1H) 5.00- 5.10 (d, 1H)

The synthetic route of 629-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2009/141090; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., Product Details of 21740-00-1

General procedure: To a stirred solution of 2-iodobenzoic acids a (10 mmol) in CH2Cl2, was added DCC (dicyclohexylcarbodiimide, 11 mmol), DMAP (Dimethylaminopyridine, 2 mmol) and alcohols b (10 mmol) in sequence. The resulting solution was stirred overnight at room temperature then filtered through a sand core funnel and washed with diethyl ether (2 x 40mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash column chromatography to obtain the pure product c in moderate to good yields. To a soluton of 2-iodobenzoates c in Et3N (5 mL) was added PdCl2 (PPh3)2 (4 mol %) and CuI (2 mol %) and the reaction vial was flushed with Ar and the reaction mixture was stirred for 5 minutes. A solution of propargyl alcohols d (1.05 equiv) in Et3N (5 mL) were then added dropwise through a syringe for 5 minutes. The resulting solution was stirred at room temperature overnight. When the reaction was considered complete as determined by TLC analysis, the mixture was quenched by addition of saturated aqueous ammonium chloride (10 mL) and extracted with ethyl ether (3 x 40 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash column chromatography to give 1.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Zhu, Hai-Tao; Tong, Xiao-Juan; Zhou, Ni-Ni; Yang, De-Suo; Fan, Ming-Jin; Tetrahedron Letters; vol. 57; 49; (2016); p. 5497 – 5500;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 98-61-3, A common heterocyclic compound, 98-61-3, name is 4-Iodobenzenesulfonyl chloride, molecular formula is C6H4ClIO2S, its 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.

A mixture of (5-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-yloxy)-acetic acid tert-butyl ester (which may be prepared as described for Intermediate 1.04; 400 mg, 1.4 mmol), diisopropylethylamine (0.46 mL, 2.6 mmol), and 4-iodobenzenesulfonyl chloride (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 414.4 mg, 1.4 mmol) in THF (10 mL) was stirred at room temperature for 14 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography, using 9% EtOAc/hexane as eluent, to give [5-(4-iodo-benzenesulfonylamino)-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-yloxy]-acetic acid tert-butyl ester (500 mg, 65%). 1H NMR (400 MHz, DMSO-d6) delta: 8.26 (d, J=7.6 Hz, 1H), 7.91 (d, J=8.1 Hz, 2H), 7.52 (d, J=8.1 Hz, 2H), 6.94-7.05 (m, 1H), 6.81 (d, J=7.6 Hz, 1H), 6.67 (d, J=8.3 Hz, 1H), 4.59 (s, 2H), 4.43 (br. s., 1H), 3.11-3.18 (m, 1H), 1.67-1.76 (m, 1H), 1.46-1.57 (m, 5H), 1.41 (s, 9H), 1.17-1.29 (m, 1H), 0.74-1.09 (m, 1H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Firooznia, Fariborz; Gillespie, Paul; Lin, Tai-An; So, Sung-Sau; US2012/309796; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 6326-42-7,Some common heterocyclic compound, 6326-42-7, name is Methyl 2-iodo-4-nitrobenzoate, molecular formula is C8H6INO4, 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.

2.140.3 methyl 4-amino-2-iodobenzoate to a mixture of ammonium chloride (122 g) and iron (38.2 g) in ethanol (1000 mL) and water (100 mL) was added Example 2.140.2 (70 g,) at room temperature. The mixture was stirred at 80 C. for 4 hours and filtered to remove insoluble material. The filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (1000 mL) and washed with water (500 mL). The aqueous phase was extracted with ethyl acetate (1000 mL*2). ;The combined organic phase was washed with brine, dried over MgSO4, filtered and concentrated to give the title compound. MS (LC-MS) m/e 278.0 (M+H)+.

The synthetic route of 6326-42-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Benatuil, Lorenzo; Bruncko, Milan; Chao, Debra; Izeradjene, Kamel; Judd, Andrew S.; Phillips, Andrew C.; Souers, Andrew J.; Thakur, Archana; (556 pag.)US2017/355769; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 188815-32-9, name is 3-Bromo-5-iodobenzoic acid, 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 188815-32-9, Safety of 3-Bromo-5-iodobenzoic acid

To a solution of 3-bromo-5-iodobenzoic acid (53, 500 mg, 1.53 mmol) in methanol (7.5 mL) was added dropwise thionyl chloride (1.1 mL, 2.18 g, 18.35 mmol) at 0 C, and then this reaction mixture was stirred at room temperature for 15 h. After being neutralized with saturated NaHCCb solution on the ice bath, the mixture was extracted with ethyl acetate (20 mL x2). The combined organic layer was washed with brine, dried over MgS04, filtered and evaporated under reduced pressure to afford compound 54 (498 mg, 96%) as a white solid; NMR (400 MHz, CDCb) d 8.32 (t, J =1.40 Hz, 1H), 8.15 (t, J =1.58 Hz, 1H), 8.06 (t, J =1.64 Hz, 1H), 3.95 (s, 3H); MS (ESI, m/z) 340.9, 342.9 [M+l]+; ESI-HRMS calcd. m/z for C8H702I79Br 340.8674, found 340.8672 [M+l]+.

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; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; JACOBSON, Kenneth A.; YU, Jinha; CIANCETTA, Antonella; WEN, Zhiwei; JUNG, Young-Hwan; (124 pag.)WO2019/157417; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com