1,3-dimethyl-1H-indole-2-carbaldehyde → 4-fluoro-1-methyl-3-(methylaminomethyl)-1H-indole

HRID 18267

Reaction equation

HRID 18267 reaction equation
BrC1C=C[C:5](NCC(OC)=O)=[N:6]C=1.[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17]([CH:25]=O)=[CH:18][N:19]2[CH3:24].CN1C2C(=CC=CC=2)C(C)=C1C=O>>[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[C:17]([CH2:25][NH:6][CH3:5])=[CH:18][N:19]2[CH3:24]

Participants

4

Reactant 3

HCID 27714681,3-dimethyl-1H-indole-2-carbaldehydeHCID 221389944-fluoro-1-methyl-1H-indole-3-carbaldehydeHCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetate

Product 1

HCID 221391514-fluoro-1-methyl-3-(methylaminomethyl)-1H-indoleYield 77%

Procedure

According to the procedure of Preparation 11 (c), except substituting 4-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 (0.2 g, 77%) was prepared as a viscous oil: MS (ES) m/e 193 (M+H)+.

Sources & evidence

ORD record
ord-ac60c99a20f64e1f897e4a31e2989145
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Linked notes

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