Dimethylformamide → HCID 71115127, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (50.4 mg, 0.173 mmol) and 4-methyl-1-(tetrahydro-2H-pyran-2-yl)-5-(tributylstannyl)-1H-pyrazole (76.9 mg, 0.169 mmol) was added N,N-dimethylformamide (1.5 mL, 19 mmol). Nitrogen gas was bubbled through the reaction mixture for 5 minutes, and then bis(tri-t-butylphosphine)palladium (11.5 mg, 0.0225 mmol), copper(I) iodide (6.1 mg, 0.032 mmol), and cesium fluoride (53.4 mg, 0.352 mmol) was added. The reaction mixture was stirred in a sealed vial at 50° C. for 2 hours, and then at 80° C. for 16 hours. The mixture was then partitioned between ethyl acetate and water, and the organic layer was washed with water and brine, dried over MgSO4, filtered, and evaporated in vacuo. The crude product was purified via flash chromatography on silica gel (12 g silica, solvent gradient: 20-100% ethyl acetate in heptanes) to yield 43.0 mg (67%) of N-(7-(4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)isoquinolin-3-yl)cyclopropanecarboxamide. LCMS (ESI): M+H=377.2.

Provenance & Evidence