Water → HCID 78135729, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(1-(3-bromo-4-(2-(methylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol (150 mg, 1.0 eq) in 5 mL DMF was added CuCN (36 mg, 1.2 eq) at rt. The mixture was then heated at 120° C. overnight, poured into water, and the resulting mixture was extracted with EtOAc. The extract was washed with water and brine, dried, concentrated, and purified by column chromatography with CH2Cl2:MeOH(NH3)=1:1 to give the desired product (10 mg, 6% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.36 (s, 1H), 6.99-7.21 (m, 7H), 6.90 (d, J=8.8 Hz, 1H), 6.81 (d, J=8.8 Hz, 1H), 6.68 (d, J=8.8 Hz, 1H), 6.49 (d, J=8.8 Hz, 1H), 4.32 (t, J=5.6 Hz, 1H), 4.20 (t, J=5.2 Hz, 1H), 3.46 (t, J=5.6 Hz, 1H), 3.30 (t, J=5.2 Hz, 1H), 3.29 (s, 3H), 2.40-2.50 (m, 2H), 0.90 (t, J=5.6 Hz, 3H); m/z=399 [M+1]+.

Provenance & Evidence