1-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one → 1-(4-(2,3-Dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinoline-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 1-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one (0.330 g, 0.820 mmol) and dicyanozinc (0.116 g, 0.984 mmol) in DMF (1.50 mL) was added 1,1′-bis(diphenylphosphino)ferrocene (0.023 g, 0.041 mmol) and Pd2(dba)3 (0.038 g, 0.041 mmol). The vial was purged with argon, sealed, and heated at 120° C. for 16 h. The mixture was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide the crude material. The crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (0.246 g, 82% yield) as an off-white solid. LCMS, [M+H]+=349.1. 1H NMR (400 MHz, CDCl3) δ 7.41 (d, J=7.7 Hz, 1H), 7.28-7.17 (m, 2H), 7.01 (t, J=7.9 Hz, 1H), 6.75 (d, J=7.5 Hz, 1H), 6.64 (d, J=8.2 Hz, 1H), 3.96 (t, J=5.6 Hz, 2H), 3.82-3.71 (m, 2H), 2.85 (s, 2H), 2.73 (t, J=7.1 Hz, 2H), 2.24 (s, 3H), 2.18 (dt, J=12.9, 6.4 Hz, 2H), 2.05-1.88 (m, 5H).

Provenance & Evidence