1,3-dimethyl-1H-indole-2-carbaldehyde → 7-Chloro-N,1-dimethyl-1H-indole-3-methanamine

HRID 1361998Notes

Reaction equation

HRID 1361998 reaction equation
BrC1C=C[C:5](NCC(OC)=O)=[N:6]C=1.[Cl:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[N:22]([CH3:24])[CH:21]=[C:20]2[CH:25]=O.CN1C2C(=CC=CC=2)C(C)=C1C=O>>[Cl:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[N:22]([CH3:24])[CH:21]=[C:20]2[CH2:25][NH:6][CH3:5]

Participants

4

Reactant 3

HCID 27714681,3-dimethyl-1H-indole-2-carbaldehydeHCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetateHCID 221391467-chloro-1-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 221390677-Chloro-N,1-dimethyl-1H-indole-3-methanamineYield 93%

Procedure

According to the procedure of Preparation 13 (c), except substituting 7-chloro-1-methyl-1H-indole-3-carboxaldehyde for the 1,3-dimethyl-1H-indole-2-carboxaldehyde, the title compound (2.0 g, 93%) was obtained as an amber oil: MS (ES) m/e 209.2 (M+H)+.

Sources & evidence

ORD record
ord-1a58c313c9e248d391ea6b78a78bf570
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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