反应详情

Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and (E)-3-(4-bromophenyl)acrylaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 11 as a white solid (95 mg, 64%). Analytical data for 11: 1H NMR (500 MHz, CDCl3) δ 9.37 (d, J=8.0 Hz, 1H), 7.89 (ddd, J=9.1, 6.1, 3.2 Hz, 1H), 7.47-7.41 (m, 2H), 7.39-7.30 (m, 3H), 7.09-7.02 (m, 1H), 7.02-6.92 (m, 5H), 4.08 (d, J=6.9 Hz, 1H), 3.56 (ddd, J=9.8, 6.8, 5.0 Hz, 1H), 3.27 (dd, J=14.9, 4.9 Hz, 1H), 2.41 (dd, J=14.9, 9.9 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 168.6, 159.1 (d, JCF=243.6 Hz), 155.4 (d, JCF=240.8 Hz), 148.9, 136.9, 136.8, 136.5, 131.7, 130.8, 129.3, 128.4, 127.9, 120.6, 118.3 (dd, JCF=12.4, 9.4 Hz), 117.1 (dd, JCF=25.7, 8.3 Hz), 116.6 (dd, JCF=24.5, 9.6 Hz), 114.5 (dd, JCF=26.9, 3.8 Hz), 110.7 (d, JCF=3.7 Hz), 47.1, 38.5, 32.3; IR (film) cm−1 1773, 1618, 1529, 1481, 1463, 1240, 1171, 1119, 1099, 1071, 1011, 765, 740, 699; LRMS (ESI): Mass calcd for [M+H]+ C25H18BrF2N2O2: 495.0. found 495.0; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 10% IPA/hexanes; 1.0 mL/min, 280 nm), Rt1 (major)=33.1, Rt2 (minor)=52.8 min; er=96:4.

1. customPrepared
2. customThe unpurified residue was purified by flash chromatography