Methanol → 7-Ethyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid
Reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([O:17][C:18]2[CH:19]=[N:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([O:14]CC)=[O:13])=[CH:8]2)[CH3:2].CO.[OH-].[K+]>O1CCCC1>[CH2:1]([C:3]1[CH:4]=[C:5]([O:17][C:18]2[CH:19]=[N:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]2)[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl 7-ethyl-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (3.64 g), methanol (20 mL), and tetrahydrofuran (40 mL) was added an aqueous solution (10 mL) of potassium hydroxide (1.6 g), and the mixture was stirred at room temperature for 4 hr. The reaction solution was concentrated, acidified with aqueous citric acid solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained pale-yellow crystals were washed with ethyl acetate-hexane to give the title compound (3.4 g, yield 100%) as pale-yellow crystals.
Workup
- concentrationThe reaction solution was concentrated
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- washThe obtained pale-yellow crystals were washed with ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-108eaf67cc034e81bba012e74dc0a245
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557805B2
Reaction notes
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