1,3-dimethyl-1H-indole-2-carbaldehyde → 1-Ethyl-5-fluoro-3-(methylaminomethyl)-1H-indole

Reaction equation

BrC1C=C[C:5](NCC(OC)=O)=[N:6]C=1.[CH2:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=2)[C:18]([CH:26]=O)=[CH:17]1)[CH3:15].CN1C2C(=CC=CC=2)C(C)=C1C=O>>[CH2:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=2)[C:18]([CH2:26][NH:6][CH3:5])=[CH:17]1)[CH3:15]

Participants

Reactant 3

HCID 27714681,3-dimethyl-1H-indole-2-carbaldehyde

HCID 221389981-ethyl-5-fluoro-1H-indole-3-carbaldehyde

HCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetate

Product 1

HCID 221390961-Ethyl-5-fluoro-3-(methylaminomethyl)-1H-indoleYield 50%

Procedure

According to the procedure of Preparation 11 (c), except substituting 1-ethyl-5-fluoro-1H-indole-3-carboxaldehyde (0.2 g, 1.9 mmole) for the 1,3-dimethyl-1H-indole-2-carboxaldehyde, the title compound (0.1 g, 50%) was prepared as a viscous oil: MS (ES) m/e 207 (M+H)+.

Sources & evidence

ORD record: ord-3a82d6836eb449eda5c2abdd257a1b1c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153652B2

Reaction notes

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