Methanol → tert-Butyl (6-phenylpyridin-3-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3A (8.3 g, 30.3 mmol) in THF (50 mL)-MeOH (50 mL) at RT was added phenylboronic acid (7.44 g, 61 mmol), PXPd (489 mg, 0.91 mmol), followed by K2CO3 (16.75 g, 121 mmol). The reaction mixture was stirred at 70° C. in a preheated oil bath for lh. After this time, the reaction mixture was cooled to RT. The reaction mixture was poured into water (100 mL), and the resultant mixture was extracted with EtOAc (3×100 mL). The combined organics were washed with saturated NaCl, dried (Na2SO4), filtered and concentrated. The resulting residue was triturated with 30% EtOAc in hexane. The solid was collected by filtration to give the title compound as an off-white solid (5.6 g, 68%). LC/MS (method A): retention time=2.83 min, (M+H)+=271.

Provenance & Evidence