1,3-dimethyl-1H-indole-2-carbaldehyde → 3-(methylaminomethyl)-1,2,7-trimethyl-1H-indole

HRID 1362009Notes

Reaction equation

HRID 1362009 reaction equation
BrC1C=C[C:5](NCC(OC)=O)=[N:6]C=1.[CH3:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH3:24])[C:17]([CH:25]=O)=[C:16]1[CH3:27].CN1C2C(=CC=CC=2)C(C)=C1C=O>>[CH3:5][NH:6][CH2:25][C:17]1[C:18]2[C:23](=[C:22]([CH3:24])[CH:21]=[CH:20][CH:19]=2)[N:15]([CH3:14])[C:16]=1[CH3:27]

Participants

4

Reactant 3

HCID 27714681,3-dimethyl-1H-indole-2-carbaldehydeHCID 176044581,2,7-trimethyl-1H-indole-3-carboxaldehydeHCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetate

Product 1

HCID 110090053-(methylaminomethyl)-1,2,7-trimethyl-1H-indoleYield 71%

Procedure

According to the procedure of Preparation 13 (c) except substituting 1,2,7-trimethyl-1H-indole-3-carboxaldehyde for the 1,3-dimethyl-1H-indole-2-carboxaldehyde, the title compound (570 mg, 71%) was obtained as an oil which slowly crystallized: MS (ES) m/e 405.4 (2M+H)+.

Sources & evidence

ORD record
ord-9f04972190e44dce8ab6675076b7171f
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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