Nitrogen → (1-Benzyl-6-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Compound 89A (150 mg, 0.36 mmol), phenylboronic acid (57 mg, 0.47 mmol) and 2N aqueous Na2CO3 (1.25 mL, 2.5 mmol) in a mixed solvent of toluene (1.5 mL) and EtOH (0.5 mL) were stirred at RT for 30 min while N2 was allowed to bubble through the mixture, and then tetrakis(triphenylphosphine)-palladium (0) (30 mg) was added. The mixture was stirred at 90° C. under N2 for 1 h. After cooling to RT, the mixture was extracted with EtOAc (15 mL×3), and organic extracts were washed with brine, dried (Na2SO4), and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc (10-50%) in hexane to give the title compound (80 mg, 67%) as a white foam.

Provenance & Evidence