Tag: M.W=200-300

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

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

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

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

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

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

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

Synthetic Route of 82998-57-0,Some common heterocyclic compound, 82998-57-0, name is 3-Iodo-4-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.

To a solution of 3-[(4-methylpiperazin-l-yl)methyl]-5-(trifluoromethyl)aniline (0.7 equiv, prepared according to literature methods) in THF under nitrogen atmosphere was added 3-Iodo-4-methyl benzoyl chloride (1 equiv, prepared from the reaction of 3-iodo-4- methylbenzoic acid and SOCl2) in THF at room temperature during 30minutes followed by drop wise addition of (i-Pr)2EtN (2 equiv) and 4-DMAP (0.2 equiv). After stirring at ambient temperature over 3h, the reaction mixture was quenched with water. The resulting mixture was extracted with ethyl acetate and formed product was isolated as HC1 salt in acetone. ESI MS m/z – (M+l) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodo-4-methylbenzoic acid, its application will become more common.

Reference:
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala; GAMPA, Venugopala Krishna; GANGANAMONI, Srinivasulu; SIRIGIREDDY, Balakrishna Reddy; ADIBHATLA, Kali Satya Bhujanga Rao; NANNAPANENI, Venkaiah Chowdary; WO2015/186137; (2015); 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., Quality Control of 3-Iodo-4,5-dimethoxybenzaldehyde

General procedure: To a solution of cycloalkenyl iodide (1.00 equiv) in Et 2 O (0.5 M) wasslowly added a solution of n-BuLi (2.44 M in hexane, 1.10 equiv) at-78 C. After stirring for 30 min at the aforementioned temperature, B(Oi-Pr)3 (1.15 equiv) and THF (total concn 0.25 M) were added andthe resulting mixture stirred for an additional 1 h at room tempera-ture. Pd(dppf)Cl2·CH2C2 (4 mol%), the cross-coupling partner (aromatic or vinylic iodide, bromide, tosylate or chloride) (0.90 equiv) andan aqueous solution of NaOH (1.5 equiv 1.00 M) were subsequentlyadded and the reaction mixture was stirred overnight. The crude ma-terial was extracted with Et2O (3 × 20 mL), washed with a saturated aqueous solution of sodium chloride (20 mL), dried over magnesiumsulfate, filtered, concentrated and purified via flash column chroma-tography.

The synthetic route of 32024-15-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baumann, Andreas N.; Eisold, Michael; Music, Arif; Didier, Dorian; Synthesis; vol. 50; 16; (2018); p. 3149 – 3160;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

20776-54-9, Name is 2-Amino-4-iodobenzoic acid, 20776-54-9, 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.

[00313] Step A: To a solution of 2-amino-4-iodobenzoic acid (2.5 g, 9.50 mmol) in DMF (10 mL) at rt under argon were added EDCI (2.18 g, 11.40 mmol), 1 – hydroxybenzotriazole (1.54 g, 11.40 mmol), DIEA (1.98 mL, 11.40 mmol), and ammonia (7.0 N solution in MeOH; 1.90 mL, 13.30 mmol). The dark solution was stirred at rt overnight and diluted with H2O until precipitate formed. The precipitate was separated by filtration, washed with H2O, and dried under high vacuum for several hours to afford 2-amino-4-iodobenzamide as a tan solid (1.3 g, 52%). LC-MS (ESI) m/z 263 (M + H)+.

Statistics shows that 2-Amino-4-iodobenzoic acid is playing an increasingly important role. we look forward to future research findings about 20776-54-9.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; LIU, Gang; CHAO, Qi; HADD, Michael, J.; HOLLADAY, Mark, W.; ABRAHAM, Sunny; SETTI, Eduardo; WO2010/99379; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com