Methylamine → 6-Methoxy-1-methyl-2-trifluoromethyl-1H-indole-3-carboxylic acid methylamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:17]([OH:19])=O)=[C:8]([C:13]([F:16])([F:15])[F:14])[N:9]2[CH3:12])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[CH3:26][NH2:27]>>[CH3:26][NH:27][C:17]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:9]([CH3:12])[C:8]=1[C:13]([F:16])([F:15])[F:14])=[O:19]Participants
4
Procedure
This material was prepared from 6-methoxy-1-methyl-2-trifluoromethyl-1H-indole-3-carboxylic acid 76f (880 mg, 3.22 mmole), oxalyl chloride (3 ml, 2.0M solution) and methylamine (5 ml, 2.0M solution) in a manner as previously described for example 16d to give 900 mg product as white solid (98% yield). 1H NMR (300 MHz, CDCl3) δ7.62 (1H, d, J=8.9 Hz), 6.88 (1H, dd, J=2.1, 8.9 Hz), 6.73 (1H, d, J=2.1 Hz), 5.80 (1H, bs), 3.88 (3H, s), 3.79 (3H, s), 3.04 (3H, d, J=4.9 Hz).
Sources & evidence
- ORD record
- ord-625512b661d942aa9e445518e3cdb6c9
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06869962B2
Reaction notes
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