Sodium Carbonate → HCID 86587977, compound

Participants

Reaction Conditions

Reaction Steps

To an Argon-purged solution of 2-(4-bromophenyl)-pent-4-enoic acid (3,5-dichloro-phenyl)-amide (1.5 g, 3.7 mmol) in toluene/EtOH (2:1 v/v, 30 mL) was added 3-cyanophenylboronic acid (0.99 g, 6.7 mmol, 1.8 eq), Pd(PPh3)4 (160 mg, 0.44 mmol, 12%), and a solution of Na2CO3 (2.12 g, 20 mmol, 5.4 eq) in 10 mL of water. The reaction mixture was heated at 90° C. for 16 h. The mixture was partitioned between EtOAc (50 mL) and 10% NaHCO3 (50 mL) and the organic phase separated. The organic phase was washed with 10% NaHCO3 (30 mL) and saturated brine (30 mL), dried (Na2SO4), and concentrated. Chromatography on silica gel (20% EtOAc/hexanes) gave 2-(3′-cyano-biphenyl-4-yl)-pent-4-enoic acid (3,5-dichloro-phenyl)-amide as a yellow oil (685 mg, 44%). 1H NMR (300 MHz, CD3OD): δ 7.93 (m, 2H), 7.81 (m, 2H), 7.66 (m, 4H), 7.49 (m, 2H), 7.12 (t, 1H), 5.89 (m, 1H), 5.21 (m, 2H), 3.76 (t, 1H), 3.11 (m, 1H), 2.73 (m, 1H).

Provenance & Evidence