Sodium Hydroxide → 7-Methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:16][C:17]2[CH:18]=[N:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([O:14]C)=[O:13])=[CH:8]2.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:16][C:17]2[CH:18]=[N:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]2Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
Methyl 7-methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylate (0.99 g) was dissolved in a mixture of tetrahydrofuran (10 mL) and methanol (10 mL). 1M Aqueous sodium hydroxide solution (5 mL) was added and the mixture was stirred at 50° C. for 45 min. The mixture was concentrated under reduced pressure. The residue was dissolved in water, and 1M hydrochloric acid was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual amorphous solid was solidified with diethyl ether to give the title compound (0.9 g, 95%) as a pale yellow solid. MS 363 (MH+).
Workup
- concentrationThe mixture was concentrated under reduced pressure
- dissolutionThe residue was dissolved in water
- addition1M hydrochloric acid was added to the mixture
- extractionThe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-82cb6cc7c63c46a18bd3664fed3b4147
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673942B2
Reaction notes
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