Potassium Carbonate → N-(5-Ethynylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide

Participants

Reaction Steps

To a stirred mixture of N-(5-formylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide (350 mg, 1.35 mmol) and K2CO3 (370 mg, 2.7 mmol) in methanol (25 mL) under N2 was added dimethyl (1-diazo-2-oxopropyl)phosphonate (310 mg, 1.62 mmol). After stirring at room temperature for three hours, the clear reaction solution was partitioned between ethyl acetate (20 mL) and 5% NaHCO3 (20 mL). The aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 210 mg (61%) of crude title compound, N-(5-ethynylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide, as an off-white solid. ESI-MS m/z: 256 (M+H)+. It was used in the next step without further purification.

Provenance & Evidence