Sodium borohydride → HCID 58009987、化合物

反応式

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH:21]=[O:22])[N:20]=[C:15]2[CH:14]=1.[BH4-].[Na+]>O1CCOCC1.CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:29])([CH3:31])[CH3:30])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][OH:22])[N:20]=[C:15]2[CH:14]=1

参加物

実験手順

6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (5.03 g, 11.5 mmol, prepared using D from Preparation #C.1. with (E)-styrylboronic acid and E) in 1,4-dioxane (65 mL) and EtOH (13 mL) was treated with NaBH4 (0.436 g, 11.5 mmol) then stirred overnight at rt. The reaction mixture was concentrated under reduced pressure then the residue was partitioned between EtOAc (125 mL) and saturated aqueous NaHCO3 (100 mL). The layers were separated then the aqueous layer was extracted with EtOAc (75 mL). The combined organic layers were extracted with brine (50 mL) then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on neutral alumina with 8:2 DCM/EtOAc then 7:3 DCM/EtOAc then finally EtOAc to give (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanol (3.19 g, 63%): LC/MS (Table 2, Method a) Rt=2.76 min; MS m/z 439 (M+H)+.