propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide}

Base Information

• Chemical Name: propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide}
• CAS No.: 1244037-16-8
• Molecular Formula: C₂₂H₁₉F₂N₅O₄S
• Molecular Weight: 487.487
• Mol file: 1244037-16-8.mol

Synonyms:propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide}

Chemical Property of propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide}

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide}

There total 10 articles about propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide} 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: 38.0%

N-(3-(1-(2,6-dichlorobenzoyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide (1312942-05-4) + 5-bromo-2-methoxypyrimidine (14001-66-2) → propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide} (1244037-16-8)

Guidance literature:

N-(3-(1-(2,6-dichlorobenzoyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide; 5-bromo-2-methoxypyrimidine; With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); In 1,4-dioxane; water; at 60 ℃;

With potassium carbonate; In methanol;

DOI:10.1016/j.ejmech.2020.112963

Reference yield:

N-[3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]propane-1-sulfonamide (918504-27-5) + (2-methoxypyrimidin-5-yl)boronic acid (628692-15-9) → propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide} (1244037-16-8)

Guidance literature:

With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In acetonitrile; at 160 ℃; for 0.0833333h; Microwave;

Reference yield:

N-[3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]propane-1-sulfonamide (918504-27-5) → propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide} (1244037-16-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine; dmap / tetrahydrofuran / 0.5 h / 0 - 20 °C

2.1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 5 h / 80 °C

3.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 2 h / 60 °C / Inert atmosphere

3.2: 2 h / 50 °C / Inert atmosphere

With dmap; bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; water;

upstream raw materials:

N-[3-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluoro-phenyl]propane-1-sulfonamide

(2-methoxypyrimidin-5-yl)boronic acid

propane-1-sulfonic acid {3-[5-bromo-1-(2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluorophenyl}amide

methanol