HCID 66897681, compound → HCID 66897529, compound
Reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([O:16]CC)=[O:15])=[CH:10]2)[CH3:3]>O1CCCC1.C(O)C.[OH-].[Na+]>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:22][CH:21]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10]2)[CH3:1]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
Ethyl 7-(1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (1.87 g) was dissolved in a mixture of tetrahydrofuran (20 mL) and ethanol (20 mL), and 1M aqueous sodium hydroxide solution (9 mL) was added to the mixture. After stirring at 60° C. for 1 h, the mixture was concentrated under reduced pressure and the residue was dissolved in water. The mixture was cooled to 0° C. and 1M hydrochloric acid (10 mL) was added. The resulting white suspension was filtered to collect a white precipitate. The precipitate was dissolved in ethyl acetate and the solution was dried over magnesium sulfate, filtered, and concentrated to give the title compound (1.81 g, 100%) as a white amorphous solid. MS 390 (MH+).
Workup
- additionwas added to the mixture
- concentrationthe mixture was concentrated under reduced pressure
- dissolutionthe residue was dissolved in water
- temperatureThe mixture was cooled to 0° C.
- addition1M hydrochloric acid (10 mL) was added
- filtrationThe resulting white suspension was filtered
- customto collect a white precipitate
- dissolutionThe precipitate was dissolved in ethyl acetate
- dry with materialthe solution was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2ff95520da944787a0c41b6f1bc4dc8a
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673942B2
Reaction notes
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