Dimethylformamide → tert-Butyl (6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

A solution of 1B (250 mg, 0.76 mmol) and zinc cyanide (88 mg, 0.75 mmol) in DMF (2.5 mL) was bubbled with argon for 10 min, then tetrakis-(triphenylphosphine)palladium(0) (65 mg, 0.057 mmol) was added and the solution was deoxygenated. The reaction mixture was then heated at 90° C. for 4 h, cooled to RT, and partitioned between EtOAc and water. The aqueous layer was separated and extracted with EtOAc (2×20 mL). The combined EtOAc extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc (0 to 60%) in hexane to give the title compound (140 mg, 67% yield) as a white solid.

Provenance & Evidence