5-fluoro-1-methyl-1H-indole-3-carbaldehyde → 5-fluoro-1-methyl-3-(methylaminomethyl)-1H-indole

HRID 1690337Notes

Reaction equation

HRID 1690337 reaction equation
BrC1C=C[C:5](NCC(OC)=O)=[N:6]C=1.[F:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH3:24])[CH:19]=[C:18]2[CH:25]=O>>[F:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH3:24])[CH:19]=[C:18]2[CH2:25][NH:6][CH3:5]

Participants

3

Reactant 2

HCID 13820095-fluoro-1-methyl-1H-indole-3-carbaldehydeHCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetate

Product 1

HCID 221390185-fluoro-1-methyl-3-(methylaminomethyl)-1H-indoleYield 35%

Procedure

According to the procedure of Preparation 11 (c), except substituting 5-fluoro-1-methyl-1H-indole-3-carboxaldehyde (0.3 g, 1.69 mmole) for the 1,3dimethyl-1H-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-969c199bc4b746199ab37d00bbb03fc7
Source dataset
uspto-grants-2012_04
Patent number
US08153652B2

Reaction notes

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