Category: iodides-buliding-blocks

Reference of 52548-14-8, 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 52548-14-8 as follows.

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), Cs2CO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dimethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-5, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. Data for A-5: 1HNMR (500 MHz, DMSO-d6) d 12.98 (br s , IH), 8.04 (s, 2H), 7.72-7.45 (m, 3H), 2.41 (s, 3H) ppm.

According to the analysis of related databases, 52548-14-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; COLEMAN, Paul, J.; SCHREIER, John, D.; WO2010/48014; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 19718-49-1, 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. 19718-49-1, name is Methyl 4-amino-3-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

INTERMEDIATE 42 Methyl 3-{[(3^-4-(tert-butoxycarbonvnmorpholin-3-yl1methvU-2-ftrimethylsilyl’)-l//- intlupsilonle-5-earbupsilonxyldleTo a stirred solution of Intermediate 41 (31.9 g, 107.4 mmol) in DMF (160 mL) was added methyl 4-amino-3-iodobenzoate (29.8 g, 107.4 mmol), lithium chloride (4.5 g, 107.4 mmol) and sodium carbonate (22.8 g, 214.8 mmol). The resulting suspension was degassed before addition of palladium acetate (0.96 g, 4.3 mmol). The reaction mixture was heated to 11O0C for 50 minutes. It was cooled to r.t, filtered through celite, and concentrated in vacuo. The resulting brown oil was partitioned between isopropyl acetate and water (150 mL each). The aqueous fraction was extracted with isopropyl acetate (2 x 15OmL). The combined organic fractions were dried (MgSO4), treated with decolourising charcoal (5% by weight of crude material) for 30 minutes at room temperature, concentrated in vacuo and then purified by column chromatography (SiO2, DCM) to give the title compound (9g, 19%) as a pale cream solid. LCMS (ES+) 469.1 (M+ Na), RT 4.62 minutes {Method ).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-amino-3-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UCB PHARMA S.A.; WO2009/71895; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

82998-57-0, name is 3-Iodo-4-methylbenzoic acid, 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. Computed Properties of C8H7IO2

Compound 5.3. Methyl 3-iodo-4-methylbenzoate. To a solution of 3-iodo-4- methylbenzoic acid (28.0 g, 0.107 mol) in MeOH (300 mL) at 0 C was carefully added concentrated H2SO4 (30 mL). The mixture was heated at 60 C overnight, then cooled and the solvent removed under reduced pressure. The residue was carefully poured onto ice-water (200 mL) and the mixture was extracted with EtOAc (500 mL). The organics was washed with water (100 mL), saturated NaHC03 (100 mL), brine (100 mL), dried (MgS04), filtered, and concentrated to yield the title compound as a brown oil (29.0 g, 98%). XH NMR (400 MHz, CDCI3) delta 8.47 (d, J= 1.7 Hz, 1H), 7.90 (dd, J= 7.9 Hz, 1.7 Hz, 1H), 7.29 (d, J= 7.9 Hz , 1H), 3.90 (s, 2H), 2.48 (s, 3H)

The synthetic route of 82998-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 624-75-9, These common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, 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.

General procedure: Starting amine (5.0 mmol) was dissolved in dry diethyl ether (17 mL) and iodoacetonitrile (5.5 mmol, 919 mg) was added dropwise under cooling. The mixture was stirred at room temperature for 3-14 days, then precipitate was filtered off, washed with diethyl ether and dried in vacuo to give the corresponding quaternary ammonium salt 2. If the solid precipitate was not formed after 7 days, the mixture was evaporated under reduced pressure. The crude product was washed with diethyl ether (3 × 15mL) and dried in vacuo. The quaternary ammonium salt 2 was used in the next step without additional purification. The corresponding quaternary ammonium salt (3.0 mmol) was heated at 150 C on oil bath in freshly distilled DMF (7 mL) in a 25 mL round-bottom flask fitted with reflux condenser and CaCl2-tube for 15 minutes. The mixture was cooled to room temperature, diluted with H2O (20 mL) and extracted with PhMe (2 × 15mL). The organic phase then was washed with H2O (2 × 15mL) and brine (15 mL), dried over Na2SO4 and evaporated in vacuo to give the desired aminoacetonitrile 4. The latter, if necessary, was purified by column chromatography (it is convenient to visualize aminoacetonitriles on TLC-plate by treating with the diluted solution of ninhydrin in EtOH). Note, that aminoacetonitriles are moisture sensitive. Products after column chromatography were additionally dried by the addition of dry PhMe (5 mL) and evaporation in vacuo.

Statistics shows that 2-Iodoacetonitrile is playing an increasingly important role. we look forward to future research findings about 624-75-9.

Reference:
Article; Buev, Evgeny M.; Smorodina, Anastasia A.; Stepanov, Maxim A.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Y.; Tetrahedron Letters; vol. 59; 17; (2018); p. 1638 – 1641;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 645-00-1,Some common heterocyclic compound, 645-00-1, name is 1-Iodo-3-nitrobenzene, molecular formula is C6H4INO2, 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: Condition B: An oven-dried pressure tube (10 mL) was charged with sodium sulfide nonahydrate (144 mg, 0.6 mmol), acetic acid (36 mg, 0.6 mmol), nitrobenzene (24.6 mg, 0.2 mmol), DMF (0.8 mL). The reaction vessel was closed under air and the resulting solution was stirred at room temperature for 20 h. Then the reaction mixture was filtered through a pad of silica gel and washed with 5 mL ethyl acetate for three times. The filtrate was removed under vacuum and the residue was purified by flash column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-3-nitrobenzene, its application will become more common.

Reference:
Article; Shuai, Qi; Li, Jun; Zhao, Feng; Su, Weike; Deng, Guojun; Chemical Papers; vol. 73; 4; (2019); p. 965 – 975;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 123158-75-8, 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 123158-75-8 as follows.

b) To a solution of 4-chloro-2-iodo-5-nitroaniline (8.5 g) in ethanol (38 ml) was added concentrated sulphuric acid (4.4 ml) dropwise, then the solution was heated to reflux and solid sodium nitrite (4.9 g) added in small amounts over 30 minutes. The mixture was refluxed a further one hour and poured into ice water, the product extracted into ethyl acetate, washed with water and brine and the organic layer was dried over sodium sulfate. The solution was evaporated and the residue purified by column chromatography to give 5-chloro-3-iodonitrobenzene (3.4 g). delta (360 MHz, DMSO-d6) 8.28 (1H, d, 2-H), 8.35 (1H, d, 6-H) and 8.46 (1H, d, 4-H).

According to the analysis of related databases, 123158-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Limited; US5270309; (1993); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 624-76-0, 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 624-76-0 as follows.

General procedure: To a solution of 5-(tert-butyl)-N-(8-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)- 2,3,4,5-tetrahydro-1H-benzo[c]azepin-5-yl)-1,2,4-oxadiazole-3-carboxamide (200 mg, 0.41 mmol) in CH3CN (20 mL) were added 2-iodoethanol (141 mg, 0.82 mmol) and K2co3(170 mg, 1.23 mmol). The mixture was stirred at 80oC for 2 h. The mixture was diluted with EtOAc (100 mL), washed with water (60 mL) and concentrated. The crude product was purified by prep- HPLC (CH3CN/H2O with 0.05% NH4Hco3as mobile phase) to give 5-(tert-butyl)-N-(2-(2- hydroxyethyl)-8-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-2,3,4,5-tetrahydro-1H- benzo[c]azepin-5-yl)-1,2,4-oxadiazole-3-carboxamide as a yellow solid (90 mg, yield: 32%). ESI-MS (M+H)+: 532.3.1H NMR (400 MHz, CD3OD) delta: 8.43 (d, J = 5.2 Hz, 1H), 8.04-8.00 (m, 3H), 7.64 (s, 1H), 7.47 (d, J = 8.0 Hz, 1H), 7.25 (d, J = 5.0 Hz, 1H), 5.60 (d, J = 9.6 Hz, 1H), 4.22-4.10 (m, 2H), 3.91 (s, 3H), 3.75 (t, J = 6.0 Hz, 2H), 3.28-3.21 (m, 2H), 2.69-2.65 (m, 2H), 2.31-2.27 (m, 1H), 2.00-1.97 (m, 1H), 1.53 (s, 9H).

According to the analysis of related databases, 624-76-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN MA INC.; HOPKINS, Brian, T.; MA, Bin; PRINCE, Robin; MARX, Isaac; LYSSIKATOS, Joseph, P.; ZHENG, Fengmei; PETERSON, Matthew; PATIENCE, Daniel, B.; (205 pag.)WO2018/191577; (2018); 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. 32024-15-0, name is 3-Iodo-4,5-dimethoxybenzaldehyde, A new synthetic method of this compound is introduced below., SDS of cas: 32024-15-0

7-Ethoxy-4-(3-iodo-4,5-dimethoxybenzyl)isoquinolin-8-ol hydrochloride 72In an ace pressure tube, 2-((2,2-diethoxyethylamino)methyl)-6-ethoxyphenol SAO 33014 (244 mg, 0.86 mmol) and 3-iodo-4,5-dimethoxybenzaldehyde RBO 40110 (250 mg, 0.86 mmol) were dissolved in a mixture EtOH:37% HCI solution = 1 :1 (10 ml_). The reaction mixture was stirred at 100C for 10 min then cooled to RT. The volatiles were removed under vacuum and the residue was taken back in EtOAc (150 ml_) and neutralized with a 10% NaHCO3 aq. solution (15 ml_). The separated organic layer was washed with water (3×30 ml_), brine (30 ml_), dried over Na2SO4, filtered and evaporated to give a yellow solid. This solid was purified by column chromatography (SiO2, eluent CH2CI2:EtOAc = 100:0 to 50:50) to give, after evaporation and drying, 7-ethoxy-4-(3-iodo-4,5-dimethoxybenzyl)isoquinolin-8-ol (37 mg). This solid was dissolved in MeOH (2 ml_) and a 0.49 N HCI solution in MeOH (160 muIota_, 0.08 mmol) was slowly added. The reaction mixture was stirred at 4C for 15 min. After evaporation and drying under P2O5, 7-ethoxy-4-(3-iodo-4,5- dimethoxybenzyl)isoquinolin-8-ol hydrochloride 72 (39 mg, 9% yield) was obtained as a yellow solid. MW: 501 .75; Yield: 9%; Yellow Solid; Mp (C): 221 .9Rf. 0.40 (CH2CI2:EtOAc = 50:50, free base).1H-NMR (CD3OD, delta): 1 .50 (t, 3H, J = 9 Hz, CH3), 3.75 (s, 3H, OMe), 3.81 (s, 3H, OMe), 4.35 (q, 2H, J = 9 Hz OCH2), 4.47 (s, 2H, CH2), 7.00 (s, 1 H, ArH), 7.23 (s, 1 H, ArH), 7.82 (d, 1 H, J = 9 Hz, ArH), 8.03 (d, 1 H, J = 9 Hz ArH), 8.09 (s, 1 H, ArH), 9.66 (s, 1 H, ArH).13C-NMR (CD3OD, delta): 15.0 (CH3), 35.9 (CH2), 56.5 (O-CH3), 60.7 (O-CH3), 66.9 (O- CH2-CH3), 93.1 , 1 15.0 (ArH), 1 16.5 (ArH), 120.5, 126.8 (ArH), 128.4 (ArH), 131 .6 (ArH), 132.6, 137.3, 137.4, 142.8 (ArH), 146.5, 147.0, 149.3, 154.2.MS-ESI m/z (% rel. Int.): 466.0 ([MH]+, 100).HPLC: Method A, XBridge column, detection UV 254 nm, RT = 4.68 min, peak area 99.0%.

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; EXONHIT S.A.; LEBLOND, Bertrand; TAVERNE, Thierry; BEAUSOLEIL, Eric; CHAUVIGNAC, Cedric; CASAGRANDE, Anne-Sophie; DESIRE, Laurent; WO2011/151423; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 82777-09-1,Some common heterocyclic compound, 82777-09-1, name is 2′-Iodo-1,1′:3′,1”-terphenyl, molecular formula is C18H13I, 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 3 Synthesis of Exemplified Compound BOl[0107] [Chem. 14] [0108] The following reagents and solvents were charged into a 100-mL recovery flask. 2 , 8-Dibromodibenzothiophene : 600 mg (1.75 mmol) ( 1 , 3-Bis (diphenylphosphino) propane ) dichloronickel ( II ) : 380 mg (0.70 mmol)Toluene: 24 mLTriethylamine : 1.46 mL After this reaction solution was heated to 90C and was then added with 1.53 mL (10.5 mmol) of 4 , 4 , 5, 5-tetramethyl- 1, 3, 2-dioxaborolane, heating was performed for 6.5 hours. After the reaction solution was cooled to room temperature, the reaction was quenched by addition of water, and an insoluble matter was removed by filtration of the reaction solution. After a reaction product in the filtrate was extracted using toluene, this extracted solution was washed with water and was then dried over sodium sulfate, followed by concentration, so that a crude product was obtained. The obtained crude product was refined by a silica gel column chromatography (eluent: toluene), and 124 mg of intermediate S-Bpin2 was obtained (yield: 16%) . [0109] Then, the following reagents and solvents were charged into a 50-mL recovery flask. 2 ‘ -Iodo-m-terphenyl: 245 mg (0.688 mmol) S-Bpin2:120 mg (0.275 mmol) Tetrakis ( triphenylphosphine ) palladium ( 0 ) : 25 mg (22 umol) Toluene: 6 mLEthanol: 3 mL 30-wt% cesium carbonate aqueous solution: 3 mL This reaction solution was heat-refluxed for 4.5 hours while being stirred in a nitrogen atmosphere. After the reaction was completed, the reaction solution was washed with water and was then dried over sodium sulfate, followed by concentration, so that a crude product was obtained.Next, this crude product was refined by a silica gel column chromatography (eluent: heptane/chloroform=3/l ) , and heating dispersion washing was further performed using a mixed solvent containing hexane and ethanol. After a crystal thus obtained was vacuum dried at 150C, sublimation refining was performed at a pressure of 10~4 Pa and a temperature of 340C, so that 120 mg of a high-purity exemplified compound B01 was obtained (yield: 68%). [0110] The result of identification of the obtainedcompound is shown below. [MALDI-TOF-MS] Observed value:[1H-N R (400 MHz, CDC13) ]delta 7.75-7.42 (m, 6H) , 7.35 (d, 2H) , 7.16-7.01 (m, 22H) , 6.85 (dd, 2H) . In addition, the Tl energy (equivalent wavelength) of the exemplified compound B01 was 423 nm measured by a method similar to that of Example 1. [0111] When the energy gap of the exemplified compound B01 was further measured by a method similar to that of Example 1, the absorption edge of the absorption spectrum was 322 nm, and the energy gap of the exemplified compound B01 was 3.85 eV. [0112] In addition, when the ionization potential of the exemplified compound B01 was measured by a method similar to that of Example 1, 6.49 eV was obtained. [0113] Furthermore, when the LUMO level of the exemplified compound B01 was estimated by a method similar to that of Example 1, it was estimated to be -2.64 eV.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2′-Iodo-1,1′:3’,1”-terphenyl, its application will become more common.

Reference:
Patent; CANON KABUSHIKI KAISHA; KOSUGE, Tetsuya; KAMATANI, Jun; KISHINO, Kengo; TOMONO, Hiroyuki; WO2011/132624; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, 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 31599-61-8, Quality Control of 4-Iodo-1,2-dimethylbenzene

14 Typical procedure for the preparation of 4,5-disubstituted-1,2,3-(NH)-triazoles (synthesis of 3a): A round-bottom sidearm flask (10 mL) containing PdCl2(PPh3)2 (0.015 mmol) was subjected to the Schlenk-line procedures of evacuation and purging of CO for three cycles. Iodobenzene and 4 equiv Et3N (1.2 mmol) were successively added, and the mixture was stirred at room temperature for 10 min, then 1-hexyne (0.45 mmol) was added, continuously stirred at room temperature for 14 h. Then NaN3 (35.1 mg, 0.54 mmol) and 1 mL DMSO were added to the mixture and the reaction continued at 45 C for 36 h. Following, to the reaction mixture was added water (2 mL), 20% HCl solution (1 mL) and extracted with ether (3 * 10 mL). The combined organic phases were washed with brine (2 * 5 mL), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was subjected to flash column chromatography with hexanes/EtOAc (5/1) as eluent to obtain the desired 3a (56.33 mg, 82% yield). All products gave satisfactory spectroscopic and analytical data.

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, 4-Iodo-1,2-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Na; Wang, Dong; Li, Jihui; Shi, Weilin; Li, Chao; Chen, Baohua; Tetrahedron Letters; vol. 52; 9; (2011); p. 980 – 982;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com