4-Bromoanisole → N-(4-Methoxyphenyl)-4-phenyl-1-naphthalenamine

Participants

Reaction Conditions

Reaction Steps

A pyrex reaction tube was charged with sodium tert-butoxide (239 mg, 2490 μmol), Pd2(dba)3 (81.4 mg, 88.9 μmol), S-Phos (146 mg, 356 μmol), 1-bromo-4-methoxybenzene (333 mg, 1779 μmol), 4-phenylnaphthalen-1-amine (390 mg, 1779 μmol) and dioxane. The tube was sealed and the mixture was stirred at 100° C. for 2 h. LCMS showed complete conversion to product. The mixture was diluted with DCM and washed with water. The organic portion was dried, filtered and concentrated. The crude material was passed through a plug of silica gel using 50% EtOAc/hex and the filtrate was concentrated to provide the desired product. MS: [M+H]=326.

Provenance & Evidence