Ethyl 7-[(1-methyl-1H-imidazol-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate → 7-[(1-Methyl-1H-imidazol-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid

HRID 1188882Notes

Reaction equation

HRID 1188882 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][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]CC)=[O:19])=[CH:14]2>O1CCCC1.C(O)C.[OH-].[Na+]>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][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]([OH:20])=[O:19])=[CH:14]2

Participants

5

Reactant 1

HCID 66898045Ethyl 7-[(1-methyl-1H-imidazol-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate

Product 1

HCID 668972847-[(1-Methyl-1H-imidazol-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acidYield 86%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 7-[(1-methyl-1H-imidazol-2-yl)methoxy]-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (100 mg) was dissolved in a mixed solvent of tetrahydrofuran (2 mL)-ethanol (2 mL), 1M aqueous sodium hydroxide solution (2 mL) was added, and the mixture was stirred at 50° C. for 50 min. The reaction. solution was allowed to cool to room temperature, and concentrated under reduced pressure. Water was added to the residue, and the mixture was neutralized with 1M hydrochloric acid. The obtained crystals were collected by filtration, and washed successively with water and diethyl ether to give the title compound (80 mg, yield 86%) as a white solid. The white solid was recrystallized from N,N-dimethylformamide-water to give colorless crystals. melting point 209-210° C. (decomposition).

Workup

  1. additionwas added
  2. customThe reaction
  3. temperatureto cool to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionWater was added to the residue
  6. filtrationThe obtained crystals were collected by filtration
  7. washwashed successively with water and diethyl ether

Sources & evidence

ORD record
ord-4a03b75561a840ac8bbc86d2e4ee0e56
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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