Dimethylformamide → HCID 67076206, compound

Participants

Reaction Steps

Palladium acetate [Pd(OAc)2] (101 mg, 0.45 mmol), (+)-BINAP (280 mg, 0.45 mmol) and dimethylformamide (70 mL) were charged to a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. The mixture was stirred under argon for 30 minutes and added to a mixture of 4-amino-N-(1-methylpiperidin-yl)-3-(trifluoromethoxy)benzamide (3.78 g, 12.5 mmol), ethyl 8-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (1.6 g, 4.16 mmol), and potassium carbonate (5.74 g, 41.6 mmol) in dimethylformamide (50 mL). The resulting mixture was stirred at 70° C. for 8 hours under argon. After cooling to room temperature, the reaction mixture was filtered on a pad of celite. The solvent was concentrated, the crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/ethanol 9/1) to afford 850 mg (45% yield) of the title compound.

Provenance & Evidence