Sodium Carbonate → HCID 24955180, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (R)—N-(3-bromo-4,5-dimethoxybenzyl)-1-phenylethanamine 112 (1.1 g, 3.15 mmol), 4-methoxyphenylboronic acid (0.48 g, 3.15 mmol, Aldrich) and 2M Na2CO3 (5.0 mL) in 10 mL of toluene was added PPh3 (83 mg, 0.315 mmol) and Pd(PPh3)4 (0.364 g, 0.315 mmol) at room temp. under N2. The reaction mixture was then heated up to 80° C. under N2 atmosphere overnight. EtOH (4 mL) was added and the reaction was continued at 80° C. for 4 hours. The reaction was cooled to room temp. and diluted with 50 mL of EtOAc and 20 mL of sat'd. NaHCO3 aq. solution. The organic phase was separated, washed with 20 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (10% EtOAc/hexane to 50% EtOAc/hexane) to afford light yellow oil as desired product (R)—N-(3-(4-Methoxyphenyl)-4,5-dimethoxybenzyl)-1-phenylethanamine 113 (0.5 g, 42%). MS (ESI, pos. ion) m/z: 378.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 10.0-10.2 (br, 2H), 6.8-7.5 (m, 9H), 6.8 (s, 1H); 6.7 (s, 1H), 3.9 (m, 1H); 3.7-3.8 (m, 1H), 3.8 (s, 3H); 3.7 (s, 3H); 3.4 (m, 1H), 3.2 (s, 3H), 1.7 (d, J=7.0 Hz, 3H).

Provenance & Evidence