Sodium Carbonate → 6,7-Dihydro-5H-cyclopenta[b]pyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-6,7-dihydro-5H-[1]pyrindine (7.1 g, 46.2 mmol), sodium carbonate (980 mg, 9.25 mmol), potassium hexacyanoferrate(II)trihydrates (7.81 g, 18.5 mmol), palladium(II) acetate (104 mg, 462 μmol) and butyldi-1-adamantylphosphine (497 mg, 1.39 mmol) was dissolved in N-methyl-2-pyrrolidinone (46.2 ml), the solution flushed with argon and heated to 160° C. for 16 hours. After cooling to 23° C., the mixture was poured into water, extracted with dichloromethane, the combined extracts dried over sodium sulphate and the solvent evaporated leaving a dark blue liquid. The crude material was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the 6,7-dihydro-5H-[1]pyrindine-3-carbonitrile as a white solid (4.82 g, 72% yield). MS (ISP): m/z=145.1 [M+H]+.

Provenance & Evidence