1,3-dimethyl-1H-indole-2-carbaldehyde → 6-fluoro-1-methyl-3-(methylaminomethyl)-1H-indole

HRID 1361982Notes

Reaction equation

HRID 1361982 reaction equation
BrC1C=C[C:5](NCC(OC)=O)=[N:6]C=1.[F: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>>[F: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 64981976-Fluoro-1-methyl-1H-indole-3-carbaldehydeHCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetate

Product 1

HCID 221391586-fluoro-1-methyl-3-(methylaminomethyl)-1H-indoleYield 35%

Procedure

According to the procedure of Preparation 11 (c), except substituting 6-fluoro-1-methyl-1H-indole-3-carboxaldehyde (0.3 g, 1.69 mmole) for the 1,3-dimethyl-1H-indole-2-carboxaldehyde, the title compound (0.11 g, 35%) was prepared as a viscous oil: MS (ES) m/e 193 (M+H)+.

Sources & evidence

ORD record
ord-59ba9010afd84602b1a6eed8ba4f8396
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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