Sodium borohydride → HCID 44466931, compound

HRID 383468Notes

Reaction equation

HRID 383468 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]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 44466648HCID 44466648, compound

Product 1

HCID 44466931HCID 44466931, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. additionwas added
  2. customThe mixture was evaporated
  3. additionwater was added
  4. extractionfollowed by extraction with EtOAc
  5. customThe crude product was purified by reversed phase flash chromatography (acetonitrile/water)

Sources & evidence

ORD record
ord-ff35667a13b040df962d79ac3df3d483
Source dataset
uspto-grants-2013_02
Patent number
US08367665B2

Reaction notes

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