Sodium borohydride → HCID 24989422, compound

HRID 216632Notes

Reaction equation

HRID 216632 reaction equation
[BH4-].[Na+].[NH2:3][C:4]([NH:6][C:7]1[NH:8][C:9]2[C:14]([C:15]=1[C:16]([NH2:18])=[O:17])=[CH:13][CH:12]=[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=[O:26])[CH:20]=1)[CH:10]=2)=[O:5]>CO.O1CCCC1>[NH2:3][C:4]([NH:6][C:7]1[NH:8][C:9]2[C:14]([C:15]=1[C:16]([NH2:18])=[O:17])=[CH:13][CH:12]=[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][OH:26])[CH:20]=1)[CH:10]=2)=[O:5]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59189810HCID 59189810, compound2×

Product 1

HCID 24989422HCID 24989422, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (0.23 g, 6.2 mmol) was added to a solution mixture of 2-aminocarbonylamino-6-(3-formylphenyl)indole-3-carboxamide (Compound 4-69, 1.0 g, 3.1 mmol) in anhydrous methanol and anhydrous tetrahydrofuran (methanol/tetrahydrofuran=1/1, 60 mL) under ice-cooling, and the mixture was stirred at room temperature overnight. After the reaction mixture was concentrated under reduced pressure, the precipitated solid was washed with water (30 mL), ethyl acetate (30 mL), and dried under reduced pressure to give the title compound (0.59 g) as a brown solid (yield 58%).

Workup

  1. temperaturecooling
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. washthe precipitated solid was washed with water (30 mL), ethyl acetate (30 mL)
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-be7bd49b556446fc9c798d2da9ee99e6
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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