1,3-dimethyl-1H-indole-2-carbaldehyde → 6-Chloro-N,1-dimethyl-1H-indole-3-methanamine

HRID 1690353Notes

Reaction equation

HRID 1690353 reaction equation
BrC1C=C[C:5](NCC(OC)=O)=[N:6]C=1.[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([CH:25]=O)=[CH:20][N:21]2[CH3:24])=[CH:17][CH:16]=1.CN1C2C(=CC=CC=2)C(C)=C1C=O>>[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([CH2:25][NH:6][CH3:5])=[CH:20][N:21]2[CH3:24])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 27714681,3-dimethyl-1H-indole-2-carbaldehydeHCID 221390206-chloro-1-methyl-1H-indole-3-carbaldehydeHCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetate

Product 1

HCID 221390396-Chloro-N,1-dimethyl-1H-indole-3-methanamineYield 93%

Procedure

According to the procedure of Preparation 13 (c), except substituting 6-chloro-1-methyl-1H-indole-3-carboxaldehyde for the 1,3-dimethyl-1H-indole-2-carboxaldehyde, the title compound (2.1 g, 93%) was obtained as an amber oil: MS (ES) m/e 209.2 (M+H)+.

Sources & evidence

ORD record
ord-488776d68e324601ae2d7b6b5b6146bc
Source dataset
uspto-grants-2012_04
Patent number
US08153652B2

Reaction notes

Loading…