7-chloro-1H-indole-3-carbaldehyde → 7-chloro-3-(methylaminomethyl)-1H-indole

HRID 1362010Notes

Reaction equation

HRID 1362010 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[NH:22][CH:21]=[C:20]2[CH:24]=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[NH:22][CH:21]=[C:20]2[CH2:24][NH:6][CH3:5]

Participants

4

Reactant 3

HCID 6439587-chloro-1H-indole-3-carbaldehydeHCID 27714681,3-dimethyl-1H-indole-2-carbaldehydeHCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetate

Product 1

HCID 221390047-chloro-3-(methylaminomethyl)-1H-indoleYield 92%

Procedure

According to the procedure of Preparation 13 (c), except substituting 7-chloro-1H-indole-3-carboxaldehyde for the 1,3-dimethyl-1H-indole-2-carboxaldehyde, the title compound (440 mg, 92%) was obtained as an off white solid: MS (ES) m/e 195.2 (M+H)+.

Sources & evidence

ORD record
ord-31ffc9774c194c049e4dafd7d93f0e0d
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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