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

HRID 18261Notes

Reaction equation

HRID 18261 reaction equation
BrC1C=C[C:5](NCC(OC)=O)=[N:6]C=1.[F:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[N:22]([CH3:24])[CH:21]=[C:20]2[CH:25]=O.CN1C2C(=CC=CC=2)C(C)=C1C=O>>[F:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[N:22]([CH3:24])[CH:21]=[C:20]2[CH2:25][NH:6][CH3:5]

Participants

4

Reactant 3

HCID 27714681,3-dimethyl-1H-indole-2-carbaldehydeHCID 221390377-Fluoro-1-methylindole-3-carboxaldehydeHCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetate

Product 1

HCID 221390667-fluoro-1-methyl-3-(methylaminomethyl)-1H-indoleYield 72%

Procedure

According to the procedure of Preparation 11 (c), except substituting 7-fluoro-1-methyl-1H-indole-3-carboxaldehyde (0.23, 1.3 mmole) for the 1,3-dimethyl-1H-indole-2-carboxaldehyde, the title compound (0.18 g, 72%) was prepared as a viscous oil: MS (ES) m/e 193 (M+H)+.

Sources & evidence

ORD record
ord-a4dc774b997848f2b92cd6333ab7d5ff
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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