Water → HCID 131724382, compound

HRID 50038Notes

Reaction equation

HRID 50038 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([CH2:15][C:16]([NH2:18])=[O:17])=[C:9]2[S:19]([C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[CH:23]=1)(=[O:21])=[O:20])(=[O:5])[CH3:4].O>O1CCCC1>[OH:5][CH:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([CH2:15][C:16]([NH2:18])=[O:17])=[C:9]2[S:19]([C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[CH:23]=1)(=[O:21])=[O:20])[CH3:4]

Participants

5

Reactant 3

HCID 962Water2×HCID 4311764Sodium borohydrideHCID 131724383HCID 131724383, compound

Product 1

HCID 131724382HCID 131724382, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.03 g, 0.0008 mol) was added to a mixture of 5-acetyl-3-(3,5-dimethylphenylsulfonyl)indole-2-carboxyamide (51) (0.30 g, 0.0008 mol) in tetrahydrofuran (8.5 mL) containing 0.1 mL of water, then reaction was refluxed for 1 hour. After cooling, water was added while stirring for a few minutes, then the mixture was extracted with ethyl acetate, washed with brine and dried. Removal of the solvent furnished 0.25 g (83%) of satisfactory pure title compound, mp 260-260° C. (ethanol).

Workup

  1. customreaction
  2. temperaturewas refluxed for 1 hour
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. customdried
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-44ffaf59d0f348d082e75cbe085e0367
Source dataset
uspto-grants-2004_03
Patent number
US06710068B2

Reaction notes

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