Methanol → Methyl 7-hydroxy-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate
Reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:23]([OH:25])=[O:24])=[C:7]([CH3:22])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[N:9]2)=[CH:4][C:3]=1[S:26]([CH:29]([CH3:31])[CH3:30])(=[O:28])=[O:27].[C:32](Cl)(=O)C(Cl)=O.CO>CN(C=O)C.ClCCl>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:23]([O:25][CH3:32])=[O:24])=[C:7]([CH3:22])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=3)=[N:9]2)=[CH:4][C:3]=1[S:26]([CH:29]([CH3:31])[CH3:30])(=[O:28])=[O:27]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
DMF (5 drops) was added to a suspension of 7-hydroxy-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (12.5 g, 27.6 mmol) in dichloromethane (120 mL). Oxalyl chloride (3.62 mL, 41.4 mmol) was added slowly. The mixture was stirred at room temperature for 1 h. Methanol (30 mL) was added, and the mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure to provide methyl 7-hydroxy-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate. This material was used without further purification. MS (m/z) 468.1 (M+H+).
Workup
- stirringthe mixture was stirred overnight at room temperature
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-a4ca43b5683c4e2f8af2d10c3bdb5a63
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658636B2
Reaction notes
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