Sodium Carbonate → HCID 178427387, compound

Participants

Reaction Conditions

Reaction Steps

In a pressure-proof container, palladium acetate (1.0 mg, 0.0044 mmol), 1,3-bis(diphenylphosphino) propane (1.8 mg, 0.0044 mmol), [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[6-iodo-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone (100 mg, 0.16 mmol), and sodium carbonate (18 mg, 0.17 mmol) were dissolved in anhydrous N,N-dimethylformamide (DMF) (0.22 ml). After triethylsilane (52 μl, 0.33 mmol) was added, the air inside the container was replaced with carbon monoxide. Then, the reaction mixture was heated at 60° C. with stirring under pressure with carbon monoxide (3 atm) for 24 hours. After the reaction mixture was cooled to room temperature, the pressure was released to ambient pressure. The reaction mixture was diluted with ethyl acetate. The sodium carbonate was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/5) to give 2-[5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazole-4-carbonyl]-1-(toluene-4-sulfonyl)-1H-indole-6-carbaldehyde as a yellow solid (80 mg, 85%).

Provenance & Evidence