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

Participants

Reaction Conditions

Reaction Steps

A solution of (6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester (250 mg, 0.76 mmol), prepared as described in Example 1B, 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 saturated aqueous NaCl, dried Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc (0 to 60%) in hexanes to give the title compound (140 mg, 67% yield) as a white solid.

Provenance & Evidence