Sodium borohydride → HCID 44466931, compound
Reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[C:9]3[C:14]([C:15]=2[C:16](=[O:20])[C:17]([NH2:19])=[O:18])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:28])[O:4][N:3]=1.[BH4-].[Na+]>CCO>[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:21]3[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=3)[C:9]3[C:14]([C:15]=2[CH:16]([OH:20])[C:17]([NH2:19])=[O:18])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:28])[O:4][N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
9 mg 2-(2-(3,5-Dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indol-3-yl)-2-oxoacetamide (Example 34) was mixed with 1 ml EtOH, 1.8 mg of NaBH4 was added and the mixture was stirred for 1.5 h. The mixture was evaporated, water was added, followed by extraction with EtOAc. The crude product was purified by reversed phase flash chromatography (acetonitrile/water) to provide 2-(2-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indol-3-yl)-2-hydroxyacetamide (E36). ES/MS m/z: 376.3 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.78 (m, 1H), 7.13-6.93 (m, 5H), 6.79 (m, 2H), 2.23, 2.21 (two s, 3H) and 1.93, 1.90 (two s, 3H).