Month: September 2021

Reference of 88-67-5, These common heterocyclic compound, 88-67-5, name is 2-Iodobenzoic acid, 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: To a stirred solution of different benzoic acids (6.42 mmol) in ethanol (3 mL) was added H2SO4 (0.1mL) and heated to reflux for 6-10 h. The reaction mixture was diluted with ethyl acetate followed by water. The organic layer was washed with saturated NaHCO3 followed by water and brine solution. The organic layer was dried over sodium sulphate, filtered and evaporated to obtain the respective ethyl benzoate derivatives.

The synthetic route of 88-67-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Prasanna, V. Laxmi; Narender; Asian Journal of Chemistry; vol. 27; 10; (2015); p. 3605 – 3608;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 351003-36-6, 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. 351003-36-6, name is 2-Fluoro-5-iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of Tributyl-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan- 3-yl]-stannane (300 mg) in N,N-dimethylformamide (12 mL) under argon was successively added 2-Fluoro-5-iodo-benzonitrile (630 mg), copper iodide (20 mg) and thentetrakis(triphenylphosphine) palladium (42 mg). The reaction was heated at lOOC under argon for 20 hours. The reaction was allowed to cool down to room temperature then water was added and the mixture was extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate and concentrated in vacuo to give a residue which was purified by chromatography on silica gel (eluent: heptanesdichloromethane, 2: 1) to give 5- [5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-2,5-dihydro-furan-3-yl]-2-fluoro-benzonitrile (182 mg) as a brown solid.1H-NMR (CDC13, 400 MHz): 7.65-7.63 (m, 2H), 7.47 (m, 2H), 7.40 (m, IH), 7.29 (m, IH), 6.40 (bs, IH), 5.30 (dd, J= 2.2 and 12.8 Hz, IH), 5.17 (m, IH) ppm. 19F-NMR (CDC13, 376 MHz): -78.11 and -104.17 ppm.

The chemical industry reduces the impact on the environment during synthesis 2-Fluoro-5-iodobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EL QACEMI, Myriem; CASSAYRE, Jerome Yves; TOUEG, Julie Clementine; RENOLD, Peter; PITTERNA, Thomas; WO2011/101229; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 167479-01-8, name is tert-Butyl (3-iodopropyl)carbamate, molecular formula is C8H16INO2, 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. Application In Synthesis of tert-Butyl (3-iodopropyl)carbamate

Step B: Methyl 2-(5-(bis(tert-butoxycarbonyl amino -4-phenylpyrimidin-2-yl -5-((tert- butoxycarbonyl)amino)pentanoateTo a mixture of 2-((5-(bis-ter?-butoxycarbonyl)amino-4-phenylpyrimidin-2-yl)) acetate (300 mg, 0.676 mmol) and tert-butyl (3-iodopropyl) carbamate (231 mg, 0.812 mmol) in THF (6 mL) at 25 C was added potassium 2-methylpropan-2-olate (1.35 mL, 1.35 mmol). The resulting mixture was stirred at 25 C for 12 h then partitioned between water (30 mL) and EtOAc (30 mL x 3). The combined organic layers were dried over a2S04 and concentrated to give the title compound. MS: m/z = 601.4 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 167479-01-8, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; MITCHELL, Helen; FRALEY, Mark, E.; COOKE, Andrew, J.; CHEN, Yi-Heng; STUMP, Craig, A.; ZHANG, Xu-Fang; MCCOMAS, Casey, C.; SCHIRRIPA, Kathy; MCWHERTER, Melody; MERCER, Swati, P.; BABAOGLU, Kerim; MENG, Dongfang; WU, Jane; LIU, Ping; WOOD, Harold, B.; BAO, Jianming; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (263 pag.)WO2015/148344; (2015); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 4387-36-4, A common heterocyclic compound, 4387-36-4, name is 2-Iodobenzonitrile, molecular formula is C7H4IN, 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.

In a clean, dry round bottom flask fitted with a reflux condenser vented through a three way valve attached to a vacuum source and nitrogen gas was added 1.56 g (6.8 mmol) of 2-iodobenzonitrile, 0.117 (0.12 mmol) of tris(dibenzylidineacetone)-dipalladium (0), 0.8 g (19 mmol) of LiCl and 0.15 g (0.5 mmol) of triphenylarsine followed by 30 ml of N-methylpyrrolidinone (NMP). The mixture was degassed and stirred for 10 minutes at which time most of the catalyst mixture had dissolved. 3.9 g (6.21 mmol) of the product of Step B was added in 10 ml of NMP and the reaction was heated to 80° C. for 90 minutes. TLC (10percent EtOAc/hexanes) indicated complete consumption of stannane (rf=0.4) and formation of the desired product (rf=0.1). The solution was cooled to room temperature and diluted with 50 ml of EtOAc. The solution was stirred with 20 ml of saturated KF for 20 minutes. The mixture was diluted with 200 ml of EtOAc and washed with water (6.x.75 ml), brine (1.x.50 ml) and was dried over MgSO4. The mixture was filtered and concentrated in vacuo and the residue was purified by Biotage Flash chromatography over silica gel eluting with 20percent EtOAc/hexanes to give 1.91 g (54percent yield) of the title compound. 300 MHz 1H NMR (CDCl3): d 1.45 (s, 9H); 3.19 (d, 2H); 4.20-4.68 (m, 4H); 5.40 (d, 1H); 7.25-7.55 (m, 12H); 7.65 (m, 2H), 7.80 (d, 2H).

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; Merck & Co., Inc.; US6353099; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1450754-38-7, These common heterocyclic compound, 1450754-38-7, name is 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine, 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.

(g) Compound 6 (400 mg, 1.6 mmol, 1.0 eq), sodium azide (125 mg, 1.92 mmol, 1.2 eq) and DMF (4 ml) were added to a reaction flask, and the temperature was raised to 70 C, and the reaction was carried out for 5 hours in the dark;Quenched with water, extracted with ethyl acetate, dried and dried to give a crude200 mg of compound 7, yield: 76%.

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 1450754-38-7.

Reference:
Patent; Suzhouguangdian Biological Technology Co., Ltd.; Ni Runyan; Wang Wei; (8 pag.)CN109369532; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 98-61-3, name is 4-Iodobenzenesulfonyl chloride, 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. Formula: C6H4ClIO2S

General procedure: A: Sulfonyl chloride (1 eq.) was dissolved in a mixture of dry DCM (0.2 M) and TEA (1.5 eq.). Amine (1.2 eq.) was added and the reaction was stirred at 20 C until completion (TLC). The solvent was removed under reduced pressure and the crude product was purified by column flash-chromatography on silica to give the sulfonamide.

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

Reference:
Article; Heinrich, Daniel M.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Silva, Shevan; Rigoreau, Laurent J.M.; Trivier, Elisabeth; Raynham, Tony; Turnbull, Andrew P.; Denny, William A.; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 738 – 744;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 877264-43-2, A common heterocyclic compound, 877264-43-2, name is (5-Fluoro-2-iodophenyl)methanol, molecular formula is C7H6FIO, 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 : Compound 10 (1.89 g, 7.5 mmol), compound 29 (2.28 g, 9 mmol), and cesium carbonate (6.1 1 g, 18.7 mmol) were combined in acetonitrile (75 mL), and heated at 80C for 18 hours. The crude suspension was added to brine (400 mL) and the resulting rust colored solids were collected by filtration and rinsed with water. The partially dried solids were recrystallized from hot acetonitrile (-200 mL) to afford compound 436 (2.37 g, 75%) as an orange solid. 1H NMR (400 MHz, DMSO-d6) delta 7.92 (dd, 1 H), 7.58 – 7.69 (m, 2 H), 7.05 (td, J = 8.65, 3.24 Hz, 1 H), 6.69 (s, 2 H), 5.27 (s, 2 H). LCMS m/z 423/425 [M+H]+.

The synthetic route of 877264-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 52548-14-8, name is 2-Iodo-5-methylbenzoic 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 52548-14-8, COA of Formula: C8H7IO2

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), CsCO3 (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-2, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. A solution of the acid (3.56 g, 17.52 mmol) in 150 mL of DCM was stirred and cooled to 00C. The solution was treated with oxalyl chloride (1.9 mL, 21.9 mmol) and DMF (68 muL, .878 mmol). The solution was slowly warmed to room temperature and stirred overnight. Solvent was concentrated and the resulting solid was azetroped with DCM and concentrated to provide A-4 as a yellow solid.

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, 2-Iodo-5-methylbenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; FLORES, Broc; SCHREIER, John, D.; WO2010/48016; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 52548-14-8,Some common heterocyclic compound, 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, molecular formula is C8H7IO2, 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.

Add 1.1 kg of acetone to the 5L reaction flask.131g 2-iodo-5-methylbenzoic acid,Stir and dissolve,Add 350g of anhydrous potassium carbonate,After heating to reflux (55-60 C) for half an hour, add 114g 1,2,3-triazole,2.4 g of cuprous iodide.The reaction was kept under reflux (55-60 C) for 8 hours, sampled, and sampled once every 1 h. After the reaction was completed, it was cooled to room temperature for filtration, and the filter cake was washed twice with 120 g of acetone to obtain a white solid at room temperature (20-30 C). The white solid was dissolved in 1.3 kg of purified water and stirred.After 30 min, hydrochloric acid was added dropwise at room temperature to adjust the pH of the system to 1.5-2.0 to obtain a large amount of white solid. It was stirred for 1-2 hours, filtered, and the filter cake was washed twice with purified water. The resulting solid was dried to dryness at 50 ± 5 C to give a crude compound.Add 1 compound of crude product, 0.2 kg of absolute ethanol and 0 kg of purified water to a 1 L reaction flask, and warm to 75-80 C.Clear, heat for half an hour, cool to 0-5 C, filter, filter cake with a cold ethanol solution rinse, to obtain a white solid compound 1 boutique.The compound 1 was placed in a blast drying oven at a temperature of 55 C ± 5 C and dried for 5 h. Sampling, sampling every 2h 1Time, until the test (rapid moisture analyzer: 105 C, 10 min) loss on drying ? 0.5%, get Suwoleisheng intermediate products -Compound 1 was fine white crystalline solid 86 g, yield: 93%. Purity: 99.91%, Cu < 5 ppm. The synthetic route of 52548-14-8 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Yangzijiang Pharmaceutical Group Co., Ltd.; Zou Yiquan; Xu Jingren; Cai Wei; Xuan Jingan; Chen Lingwu; Ji Ye; Zhu Yunlong; Liu Jinfeng; Hu Tao; (8 pag.)CN109810067; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 159217-89-7, name is tert-Butyl (4-iodophenyl)carbamate, molecular formula is C11H14INO2, 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. Computed Properties of C11H14INO2

fert-Butyl 4-iodophenylcarbamate (prepared using the method described in Bioorganic and Med. Chem. Lett, 2000, 8, 1203; 1.77 g, 5.55 mmol) and trans-dichlorobis (triphenylphosphine) palladium (II) (195 mg, 0.28 mmol) were weighed into a flask. The flask was degassed and placed under argon, and 1,4-dioxane (30 ml) was added. The hexamethylditin (2.00 g, 6.10 mmol) was dissolved in 5 ml of 1 ,4-dioxane, and the solution was added to the mixture. The suspension was heated at 90 C for ca. 16 h. The mixture was adsorbed onto silica gel and concentrated under vacuum. The material was purified by flash chromatography on silica gel using 1% EtOAc/hexanes to give 860 mg of the desired product. NMR: 0.23 (s, 9H), 1.47 (s, 9H), 7.33 (d, 2H), 7.42 (d, 2H), 9.28 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 159217-89-7, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/92599; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com