5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole-3-carboxamide

Base Information

• Chemical Name: 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole-3-carboxamide
• CAS No.: 1373845-06-7
• Molecular Formula: C₂₄H₂₇BFN₃O₃
• Molecular Weight: 435.306
• Mol file: 1373845-06-7.mol

Synonyms:5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole-3-carboxamide

Chemical Property of 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole-3-carboxamide

There total 2 articles about 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole-3-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: 48.0%

5-cyclopropyl-2-(4-fluorophenyl)-6-iodo-N-methyl-2H-indazole-3-carboxamide (1373839-73-6) + bis(pinacol)diborane (73183-34-3) → 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole-3-carboxamide (1373845-06-7)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dimethyl sulfoxide; at 100 ℃; for 16h; Inert atmosphere;

Reference yield:

6-amino-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide (1373845-50-1) → 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole-3-carboxamide (1373845-06-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / -10 - -5 °C

1.2: 1.5 h / 0 °C

2.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 16 h / 100 °C / Inert atmosphere

With hydrogenchloride; potassium acetate; sodium nitrite; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; dimethyl sulfoxide; 2.1: Suzuki Coupling;

Reference yield: 93.0%

2,4,5-tribromo-1-ethyl-1H-imidazole (31250-75-6) + 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole-3-carboxamide (1373845-06-7) → 5-cyclopropyl-6-(4,5-dibromo-1-ethyl-1H-imidazol-2-yl)-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide (1373845-08-9)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 100 ℃; for 16h; Inert atmosphere;

upstream raw materials:

5-cyclopropyl-2-(4-fluorophenyl)-6-iodo-N-methyl-2H-indazole-3-carboxamide

bis(pinacol)diborane

6-amino-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide

Downstream raw materials:

5-cyclopropyl-6-(4,5-dibromo-1-ethyl-1H-imidazol-2-yl)-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide

5-cyclopropyl-6-(1-ethyl-1H-imidazol-2-yl)-2-(4-fluorophenyl)-N-methyl-2H-indazole-3-carboxamide