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-(2-methoxyphenyl)acrylaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 10 as an off-white solid (81 mg, 61%). Analytical data for 10: 1H NMR (500 MHz, CDCl3) δ 9.34 (d, J=8.1 Hz, 1H), 7.89 (ddd, J=9.2, 6.0, 3.2 Hz, 1H), 7.38-7.29 (m, 3H), 7.27-7.21 (m, 1H), 7.09-7.00 (m, 3H), 7.00-6.92 (m, 1H), 6.91 (dd, J=7.6, 1.8 Hz, 1H), 6.86 (ap t, J=7.5 Hz, 2H), 4.06 (d, J=6.9 Hz, 1H), 3.84 (ddd, J=8.9, 6.9, 5.2 Hz, 1H), 3.80 (s, 3H), 3.26 (dd, J=14.2, 5.2 Hz, 1H), 2.49 (dd, J=14.2, 8.8 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 169.4, 159.1 (d, JCF=243.7 Hz), 157.8, 155.3 (d, JCF=240.5 Hz), 148.9, 137.6, 136.1, 131.9, 129.1, 128.1, 128.0, 126.0, 120.2, 117.1 (dd, JCF=25.8, 8.7 Hz), 116.4 (dd, JCF=24.7, 9.4 Hz), 114.5 (dd, JCF=27.5, 3.0 Hz), 111.3 (d, JCF=2.9 Hz), 110.1, 55.2, 44.8, 39.0, 29.1; IR (film) cm−1 1773, 1637, 1482, 1464, 1243, 1173, 1122, 1101, 1030, 813, 765, 738, 700; LRMS (ESI): Mass calcd for [M+H]+ C26H21F2N2O3: 447.1. found 447.4; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 5% IPA/3% MeOH/hexanes 0.5 mL/min, 280 nm), Rt1 (minor)=32.2, Rt2 (major)=42.5 min; er=96:4.

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