[4-[(2-fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]-(3-hydroxyazetidin-1-yl)methanone

Base Information

• Chemical Name: [4-[(2-fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]-(3-hydroxyazetidin-1-yl)methanone
• CAS No.: 1203663-26-6
• Molecular Formula: C₁₇H₁₄FIN₄O₂
• Molecular Weight: 452.227

Synonyms:[4-[(2-fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]-(3-hydroxyazetidin-1-yl)methanone

Chemical Property of [4-[(2-fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]-(3-hydroxyazetidin-1-yl)methanone

Chemical Property:

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Technology Process of [4-[(2-fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]-(3-hydroxyazetidin-1-yl)methanone

There total 7 articles about [4-[(2-fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]-(3-hydroxyazetidin-1-yl)methanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 49.0%

4-[(2-fluoro-4-iodophenyl)amino]-1H-indazole-5-carboxylic acid (1203662-71-8) + azetion-3-ol hydrochloride (18621-18-6) → [4-[(2-fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]-(3-hydroxyazetidin-1-yl)methanone (1203663-26-6)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

Reference yield:

4-bromo-1H-indazole-5-carboxylic acid tert-butyl ester (1203662-37-6) → [4-[(2-fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]-(3-hydroxyazetidin-1-yl)methanone (1203663-26-6)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 18 h / 20 °C

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 4 h / Inert atmosphere; Heating

3: Iodine monochloride / dichloromethane / 0.25 h / 0 °C

4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; Iodine monochloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm2017094

Reference yield:

4-bromo-indazole-1,5-dicarboxylic acid di-tert-butyl ester (1203662-32-1) → [4-[(2-fluoro-4-iodophenyl)amino]-1H-indazol-5-yl]-(3-hydroxyazetidin-1-yl)methanone (1203663-26-6)

Guidance literature:

Multi-step reaction with 4 steps

1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 4 h / Inert atmosphere; Heating

2: Iodine monochloride / dichloromethane / 0.25 h / 0 °C

3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; Iodine monochloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm2017094

upstream raw materials:

4-[(2-fluoro-4-iodophenyl)amino]-1H-indazole-5-carboxylic acid

azetion-3-ol hydrochloride

2-bromo-4-fluorobenzoic acid tert-butyl ester

4-(2-fluoro-4-iodophenylamino)-indazole-1,5-dicarboxylic acid di-tert-butyl ester

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