Ethanol → HCID 67196418, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-chloro-3-(4-fluorophenyl)-imidazo[1,5-a]pyrazine (612 mg, 2.47 mmol), DIPEA (500 μL, 2.9 mmol), Pd[PhCN]2Cl2 (25 mg, 0.07 mmol), and dppf (50 mg, 0.09 mmol) in absolute ethanol (10 mL) in a pressure reactor with stirring and placed under 15 bars of carbon monoxide is warmed at 80° C. After 24 hours, the mixture is cooled to room temperature, returned to atmopheric pressure and opened. The mixture is diluted with brine (100 mL) and extracted with EtOAc (3×40 mL). The combined organic layers are washed with brine (3×25 mL), dried over magnesium sulfate, filtered and concentrated. The residue is passed through a pad of silica gel using dichloromethane-heptane (1:1) to load the sample and then eluting with dichloromethane-heptane (1:1, then 75:25, then 100:0) and then EtOAc-dichloromethane (2:8, then 1:1) to afford 3-(4-fluorophenyl)-imidazo[1,5-a]pyrazine-8-carboxylic acid ethyl ester.

Provenance & Evidence