5-methoxy-1-methyl-1H-indole-3-carbaldehyde → 1-(5-Methoxy-1-methyl-1H-indol-3-yl)-N-methylmethanamine

Reaction equation

BrC1C=C[C:5](NCC(OC)=O)=[N:6]C=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH3:25])[CH:20]=[C:19]2[CH:26]=O.CN1C2C(=CC=CC=2)C(C)=C1C=O>>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([CH3:25])[CH:20]=[C:19]2[CH2:26][NH:6][CH3:5]

Participants

Reactant 3

HCID 9259735-methoxy-1-methyl-1H-indole-3-carbaldehyde

HCID 27714681,3-dimethyl-1H-indole-2-carbaldehyde

HCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetate

Product 1

HCID 122838821-(5-Methoxy-1-methyl-1H-indol-3-yl)-N-methylmethanamineYield 98%

Procedure

According to the procedure of Preparation 13 (c), except substituting 5-methoxy-1-methyl-1H-indole-3-carboxaldehyde for the 1,3-dimethyl-1H-indole-2-carboxaldehyde, the title compound (0.85 g, 98%) was obtained as a light yellow oil: MS (ES) m/e 205.2 (M+H)+.

Sources & evidence

ORD record: ord-a0a8d5a420004846b85b90df8251267c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741339B2

Reaction notes

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