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-(furan-2-yl)acrylaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 16 as an off-white solid (80 mg, 66%). Analytical data for 16: 1H NMR (500 MHz, CDCl3) δ 9.45 (d, J=8.1 Hz, 1H), 7.90 (ddd, J=9.2, 6.1, 3.2 Hz, 1H), 7.37 (ap d, J=1.2 Hz, 1H), 7.37-7.27 (m, 3H), 7.11-7.01 (m, 3H), 7.01-6.94 (m, 1H), 6.34 (dd, J=3.2, 1.9 Hz, 1H), 6.02 (d, J=2.9 Hz, 1H), 4.20 (d, J=6.9 Hz, 1H), 3.70 (ddd, J=10.3, 6.8, 4.1 Hz, 1H), 3.30 (ddd, J=15.9, 4.2, 1.2 Hz, 1H), 2.48 (dd, J=15.8, 10.4 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 168.4, 159.1 (d, JCF=243.8 Hz), 155.4 (dd, JCF=241.2, 2.2 Hz), 151.8, 149.1, 141.6, 136.7, 136.5, 129.2, 128.3, 128.0, 118.4 (dd, JCF=12.8, 9.2 Hz), 117.1 (dd, JCF=25.6, 8.8 Hz), 116.6 (dd, JCF=24.9, 9.6 Hz), 114.5 (dd, JCF=26.9, 3.7 Hz), 110.7 (d, JCF=3.9 Hz), 110.4, 107.6, 44.9, 38.5, 25.6; IR (film) cm−1 1770, 1636, 1620, 1529, 1482, 1464, 1452, 1173, 1117, 1008, 919, 902, 885, 875, 814, 766, 736, 700; LRMS (ESI): Mass calcd for [M+H]+ C23H17F2N2O3: 407.1. found 407.3; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 5% IPA/3% MeOH/hexanes 0.5 mL/min, 280 nm), Rt1 (major)=32.4, Rt2 (minor)=36.4 min; er=98:2.

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