(2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide

Base Information

• Chemical Name: (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide
• CAS No.: 1346172-63-1
• Molecular Formula: C₃₀H₃₄ClF₃N₆O₄SSi
• Molecular Weight: 695.237
• Mol file: 1346172-63-1.mol

Synonyms:(2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide

Chemical Property of (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide

There total 11 articles about (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide 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:

5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (866546-11-4) + (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-chloropyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide (1346172-62-0) → (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide (1346172-63-1)

Guidance literature:

With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

Reference yield:

5-chloro-2-pyridylamine (1072-98-6) → (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide (1346172-63-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: iodine; sulfuric acid; periodic acid / ethanol; water / 15 h / 80 °C

1.2: pH 9

2.1: triethylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 1.67 h / 20 - 40 °C / Inert atmosphere

3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 4 h / 80 °C / Inert atmosphere

4.1: bromine; acetic acid / 3 h / 90 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.83 h / 0 °C / Inert atmosphere

5.2: 1.5 h / 0 - 25 °C

6.1: potassium acetate / palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,2-dimethoxyethane / 6 h / 86 °C / Inert atmosphere

7.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

With copper(l) iodide; sulfuric acid; potassium tert-butylate; bromine; iodine; potassium acetate; sodium hydride; sodium carbonate; acetic acid; periodic acid; triethylamine; bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; mineral oil;

Reference yield:

2-amino-5-chloro-3-[(trimethylsilyl)ethynyl]pyridine (866318-90-3) → (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-(6-(5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)azetidine-2-carboxamide (1346172-63-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 4 h / 80 °C / Inert atmosphere

2.1: bromine; acetic acid / 3 h / 90 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.83 h / 0 °C / Inert atmosphere

3.2: 1.5 h / 0 - 25 °C

4.1: potassium acetate / palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,2-dimethoxyethane / 6 h / 86 °C / Inert atmosphere

5.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

With potassium tert-butylate; bromine; potassium acetate; sodium hydride; sodium carbonate; acetic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; 1,2-dimethoxyethane; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

5-chloro-2-pyridylamine

5-chloro-3-iodo-2-aminopyridine

2-amino-5-chloro-3-[(trimethylsilyl)ethynyl]pyridine

3-bromo-5-chloro-1 H-pyrrolo[2,3-b]pyridine