Sodium borohydride → HCID 67300527, compound

HRID 1015448Notes

Reaction equation

HRID 1015448 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([N:19]=[C:20]([NH2:22])[NH2:21])=[O:18])=[CH:14][CH:15]=2)[C:10]([CH:23]=[O:24])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([N:19]=[C:20]([NH2:22])[NH2:21])=[O:18])=[CH:14][CH:15]=2)[C:10]([CH2:23][OH:24])=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86628481HCID 86628481, compound

Product 1

HCID 67300527HCID 67300527, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 415 mg portion of 1-benzyl-N-(diaminomethylene)-3-formyl-1H-indole-5-carboxamide was suspended in 15 ml of methanol, 98 mg of sodium borohydride was added at 0° C., followed by stirring at room temperature for 1.5 hours. After evaporation of the solvent and subsequent addition of water, the thus precipitated solid was purified by silica gel column chromatography (Clomatorex (registered trademark), methanol:chloroform:water=50:1:0.1 to 30:1:0.1 to 20:1:0.1 to 10:1:0.1). The thus obtained product was crystallized from methanol/water to obtain 325 mg of 1-benzyl-N-(diaminomethylene)-3-hydroxymethyl-1H-indole-5-carboxamide as a pale pink solid.

Workup

  1. customAfter evaporation of the solvent and subsequent addition of water
  2. customthe thus precipitated solid was purified by silica gel column chromatography (Clomatorex (registered trademark), methanol:chloroform:water=50:1:0.1 to 30:1:0.1 to 20:1:0.1 to 10:1:0.1)
  3. customThe thus obtained product was crystallized from methanol/water

Sources & evidence

ORD record
ord-cf6f2ecd70e344b1845ed3a7bc755563
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

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