Dichloromethane → Ethyl 4'-[(1R)-1-(methylamino)-2-(4-morpholinyl)ethyl]-4-biphenylcarboxylate

Participants

Reaction Steps

[(1R)-1-(4-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamine (20.0 g, 66.9 mmol) was dissolved in EtOH (500 mL) at room temperature with magnetic stirring. The resulting solution was treated with {4-[(ethyloxy)carbonyl]phenyl}boronic acid (14.5 g, 73.6 mmol) followed by K2CO3 (27.7 g, 200.7 mmol) and PdCl2(dppf)2.CH2Cl2 (2.73 g, 3.34 The reaction was maintained at 80° C. overnight. The reaction mixture was cooled to room temperature and then filtered through celite. The filtrate was concentrated and then partitioned between EtOAc and brine. The organic layer was dried over MgSO4, and filtered. The filtrate was concentrated to give the title compound as a brown oil (26.5 g, 80% purity). MS (ES) m/e 369 [M+H]−.

Provenance & Evidence