Sodium cyanoborohydride → (6,4'-Dimethoxy-biphenyl-3-ylmethyl)-[1-(1-methyl-1H-indol-4-yl)-ethyl]-amine

HRID 1072246

Reaction equation

HRID 1072246 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:7][C:6]([CH2:17][NH:18][CH:19]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=[CH:23][CH:22]=2)[CH3:20])=[CH:5][CH:4]=1.CN1C2C(=C(C(N)C)C=CC=2)C=C1.COC1C(C2C=CC(OC)=CC=2)=CC(C=O)=CC=1.C([BH3-])#N.[Na+]>>[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:7][C:6]([CH2:17][NH:18][CH:19]([C:21]2[CH:22]=[CH:27][CH:26]=[C:25]3[C:30]=2[CH:29]=[CH:28][N:24]3[CH3:23])[CH3:20])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 208032231-(1-Methyl-1H-indol-4-yl)ethan-1-amineHCID 223911916,4'-Dimethoxybiphenyl-3-carbaldehydeHCID 22391337(6,4'-Dimethoxybiphenyl-3-ylmethyl)-(1-quinolin-4-yl-ethyl)-amine

Product 1

HCID 22391223(6,4'-Dimethoxy-biphenyl-3-ylmethyl)-[1-(1-methyl-1H-indol-4-yl)-ethyl]-amineYield 74%

Procedure

The title compound was prepared by the same procedure for (6,4′-dimethoxy-biphenyl-3-ylmethyl)-(1-quinolin-4-yl-ethyl)-amine from 1-(1-Methyl-1H-indol-4-yl)-ethylamine (522 mg, 3.0 mmol), 6,4′-Dimethoxy-biphenyl-3-carbaldehyde (242 mg, 1.0 mmol) and sodium cyanoborohydride (1.0 g, 16 mmol, Aldrich). The title compound was purified by column chromatography (silica gel, hexane/ethyl acetate 3/2) in form as white solid in 74% yield (296 mg, 0.74 mmol).

Workup

  1. customThe title compound was purified by column chromatography (silica gel, hexane/ethyl acetate 3/2) in form as white solid in 74% yield (296 mg, 0.74 mmol)

Sources & evidence

ORD record
ord-44276e227fb04c968fe94ddb241ac5f1
Source dataset
uspto-grants-2005_06
Patent number
US06908935B2

Linked notes

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