Ethyl 7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate → Ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate
Reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]2)C1C=CC=CC=1>O1CCCC1.C(O)C.[C].[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]2Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
Ethyl 7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (0.40 g) was dissolved in a mixed solvent of tetrahydrofuran (5 mL)-ethanol (5 mL), 10% palladium-carbon (50% containing water, 0.80 g) was added, and the mixture was stirred at room temperature for 4 hr under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was crystallized from diethyl ether, and the obtained solid was washed with a mixed solvent of diethyl ether-hexane to give the title compound (0.31 g, yield 96%) as a pale-yellow solid. The pale-yellow solid was recrystallized from ethanol-hexane to give pale-yellow crystals. melting point 197-198° C.
Workup
- additionwas added
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was crystallized from diethyl ether
- washthe obtained solid was washed with a mixed solvent of diethyl ether-hexane
Sources & evidence
- ORD record
- ord-ca5e83c6fb0e43ae9308687365357842
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673942B2
Reaction notes
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