Sodium borohydride → HCID 69915601, compound

HRID 352537Notes

Reaction equation

HRID 352537 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]=[N:7][NH:8][C:9]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH3:20])=[CH:17][C:16]([Cl:21])=[CH:15][CH:14]=3)=[O:10])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][NH:8][C:9]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH3:20])=[CH:17][C:16]([Cl:21])=[CH:15][CH:14]=3)=[O:10])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 85069354HCID 85069354, compound

Product 1

HCID 69915601HCID 69915601, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-chloro-3-methyl-indole-2-carboxylic acid (4-methylbenzylidene)-hydrazide (7 mg, 0.022 mmol) in a mixture of methanol (8.5 mL) and water (1.5 mL) at 50° C. was added sodium borohydride (1.62 mg, 0.044 mmol). It was stirred for 4 h and the solution was evaporated. The residue was purified by column chromatography (silica gel, EtOAc/Hexane=4:1) to give 4 mg (56%) of the title compound. 1H NMR (CD3OD): 7.42 (s, 1H), 7.22−7.19 (m, 3H), 7.07−7.03 (m, 3H), (bs, 1H), 3.91 (s, 2H), 2.27 (s, 3H), 2.20 (s, 3H).

Workup

  1. customthe solution was evaporated
  2. customThe residue was purified by column chromatography (silica gel, EtOAc/Hexane=4:1)

Sources & evidence

ORD record
ord-b3605360f87b429eb05d69106f96b0a1
Source dataset
uspto-grants-2004_06
Patent number
US06747052B2

Reaction notes

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