Methyl iodide → 6-Methoxy-1-methyl-2-trifluoromethyl-1H-indole-3-carboxylic acid Ethyl Ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[NH:8][C:7]=1[C:17]([F:20])([F:19])[F:18])=[O:5])[CH3:2].[H-].[Na+].[CH3:23]I>>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[N:8]([CH3:23])[C:7]=1[C:17]([F:20])([F:18])[F:19])=[O:5])[CH3:2]Participants
4
Procedure
This material was prepared from 6-methoxy-2-trifluoromethyl-1H-indole-3-carboxylic acid ethyl ester 76d (1.64 9, 5.7 mmole) by treatment with NaH (274 mg, 60% in mineral oil, 6.84 mmole) and methyl iodide (1.21 g, 8.55 mmole) and NaH in a manner as previously described for example 16b to give 1.5 g product (87% yield). 1H NMR (300 MHz, CDCl3) δ7.96 (1H, dd, J=3.7, 8.8 Hz), 6.94 (1H, dd, J=2.3, 9.1 Hz), 6.77 (1H, d, J=2.1 Hz), 4.40 (2H, m), 3.89 (3H, s), 3.86 (3H, s), 1.41 (3H, m).
Sources & evidence
- ORD record
- ord-87d9dbd3aa04446ba458f528f8c6ebe9
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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