Sodium cyanoborohydride → (6,4'-Dimethoxy-biphenyl-3-ylmethyl)-[1-(1-methyl-2,3-dihydro-1H-indol-4-yl)-ethyl]-amine

HRID 2113131Notes

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]NC(C2C3C(=CC=CC=3)N=CC=2)C)=[CH:5][CH:4]=1.[CH3:31][N:32]1[C:40]2[C:35](=[C:36]([CH:41]([NH2:43])[CH3:42])[CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33]1.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:43][CH:41]([C:36]2[CH:37]=[CH:38][CH:39]=[C:40]3[C:35]=2[CH2:34][CH2:33][N:32]3[CH3:31])[CH3:42])=[CH:5][CH:4]=1

Participants

Reactant 4

HCID 5003444Sodium cyanoborohydride

HCID 208032241-(1-Methyl-2,3-dihydro-1H-indol-4-yl)-ethylamine

HCID 223911916,4'-Dimethoxybiphenyl-3-carbaldehyde

HCID 22391337(6,4'-Dimethoxybiphenyl-3-ylmethyl)-(1-quinolin-4-yl-ethyl)-amine

Product 1

HCID 22391549(6,4'-Dimethoxy-biphenyl-3-ylmethyl)-[1-(1-methyl-2,3-dihydro-1H-indol-4-yl)-ethyl]-amineYield 55%

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-2,3-dihydro-1H-indol-4-yl)-ethylamine (528 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, ethyl acetate) in form as white solid in 55% yield (221 mg, 5.5 mmol).

Workup

customThe title compound was purified by column chromatography (silica gel, ethyl acetate) in form as white solid in 55% yield (221 mg, 5.5 mmol)

Sources & evidence

ORD record: ord-8595580505744c2cbf9f46b3e9575276
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524873B2

Reaction notes

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