Sodium borohydride → 1-[5-(2,6-dimethyl-phenyl)-1-(6-isopropoxy-pyridazin-3-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol
反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:17]([C:18](=[O:24])[CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:16][N:15]([C:25]3[N:26]=[N:27][C:28]([O:31][CH:32]([CH3:34])[CH3:33])=[CH:29][CH:30]=3)[C:12]2=[CH:13][N:14]=1.[BH4-].[Na+]>C(O)C.O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:17]([CH:18]([OH:24])[CH:19]([CH2:20][CH3:21])[CH2:22][CH3:23])=[CH:16][N:15]([C:25]3[N:26]=[N:27][C:28]([O:31][CH:32]([CH3:34])[CH3:33])=[CH:29][CH:30]=3)[C:12]2=[CH:13][N:14]=1参加物
4
反応物 2
生成物 1
試薬・触媒・溶媒 1
実験手順
To a solution of 1-[5-(2,6-dimethyl-phenyl)-1-(6-isopropoxy-pyridazin-3-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one (70 mg, 0.15 mmol) in a (4:1) EtOH—H2O mixture (5 mL) −30° C., NaBH4 (50 mg, 1.3 mmol) is added, and the mixture is allowed to gradually warm up to room temperature at which the stirring is continued for 2 h. The mixture is concentrated under reduced pressure. The residue is diluted with a saturated aqueous solution of Rochelle's salt (10 mL), and the product is extracted with DCM. The combined organic solutions are washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Chromatography of the residue on silica gel (hexane-EtOAc, 1:1) gives 1-[5-(2,6-dimethyl-phenyl)-1-(6-isopropoxy-pyridazin-3-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-ol as colorless oil. 1H NMR (CDCl3) 9.52 (s, 1H), 7.83 (s, 1H), 7.71 (s, 1H), 7.69 (s, 1H), 7.59 (s, 1H), 7.22-7.10 (m, 3H), 5.62 (m, 1H), 5.21 (m, 1H), 2.08 (s, 6H), 1.47 (d, J=7 Hz, 6H), 1.08 (s, 9H); LCMS m/z 459.14 (2.48 min).