Sodium borohydride → Racemic 1-{3-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}ethanol
Reaktionsgleichung
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:19]=[C:20]([C:24](=[O:26])[CH3:25])[CH:21]=[CH:22][CH:23]=4)=[CH:14][N:13]3[CH:27]=2)=[CH:6][CH:5]=1>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:18]4[CH:19]=[C:20]([CH:24]([OH:26])[CH3:25])[CH:21]=[CH:22][CH:23]=4)=[CH:14][N:13]3[CH:27]=2)=[CH:8][CH:9]=1Komponenten
4
Versuchsvorschrift
164 mg of sodium borohydride are added portionwise to 150 mg of 1-{3-[2-(4-chloro-phenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}ethanone (compound obtained in 8.1) dissolved in 20 ml of methanol. The mixture is then stirred at ambient temperature for one hour and the solvent is then evaporated off under reduced pressure. The residue is taken up in between water and dichloromethane, the organic phase is separated by settling out and dried over sodium sulphate and the solvent is then evaporated off under reduced pressure. The residue is triturated in diisopropyl ether and recovered by filtration and then dried in a dessicator under reduced pressure. 124 mg of compound are obtained. Mp=174-176° C. 1H NMR (DMSO-d6, δ in ppm): 1.37 (d, J=6.5 Hz, 3H); 4.79 (m, 1H); 5.19 (d, J=4.2 Hz, 1H); from 7.31 to 7.69 (m, 8H); 7.97 (m, J=8.6 Hz, 2H); 8.41 (s, 1H); 8.84 (m, 1H). M+H=349.