Dichloromethane → HCID 492682、化合物

反応式

C(Cl)Cl.[F:4][C:5]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:6]=1[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([CH2:17][OH:18])[C:11]=2[N:10]=[C:9]1[C:19]1[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=1[F:26]>N1C=CC=CC=1.N1C=CC=CC=1.C(Cl)Cl>[F:4][C:5]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:6]=1[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([CH:17]=[O:18])[C:11]=2[N:10]=[C:9]1[C:19]1[C:20]([F:26])=[CH:21][CH:22]=[CH:23][C:24]=1[F:25]

参加物

実験手順

To CrO3 (1.26 g) dissolved in pyridine (1.0 mL) and CH2Cl2 (9.0 mL) was added 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-4-hydroxylmethylbenzimidazole (Example 112) (0.49 g, 1.27 mmol) dissolved in pyridine:CH2Cl2 (1:1) (2 mL). After stirring for 6 h, the reaction was filtered. The filtrate was diluted with CH2Cl2, and washed with NaHCO3 (sat. soln) and NaCl (sat. aq). The combined washings were dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash chromatography eluting with 1% methanol/CH2Cl2. Recrystallization from diethylether:hexane (3:1) yielded white crystals of 1-(2,6-Difluorobenzyl)-2-(2,6-difluorophenyl)-benzimidazole-4-carbaldehyde (0.38 g, 0.99 mmol, 78% yield). M.p. 151-153° C. 1H-NMR (300 MHz, CD2Cl2): δ 10.82 (d, J=0.6 Hz, 1H, CHO), 7.83 (dd, J=7.5, 1.1 Hz, 1H, H7), 7.78 (dd, J=8.1, 1.1 Hz, H5), 7.58 (m, 1H, H4′), 7.44 (ddd, J=8.1, 7.5, 0.6 Hz, 1H, H6), 7.27 (m, 1H, H4″), 7.11 (m, 2H, H3′,5′), 6.84 (m, 2H, H3″,5″), 5.42 (s, 2H, CH2PhF2).