Water → tert-Butyl 5-fluoro-1-(methylsulfonyl)-1H-indole-3-carboxylate

HRID 624661Notes

Reaction equation

HRID 624661 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:26]([CH3:25])(=[O:28])=[O:27])[CH:6]=[C:5]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90031295tert-butyl 5-fluoro-1H-indole-3-carboxylate

Product 1

HCID 90031845tert-Butyl 5-fluoro-1-(methylsulfonyl)-1H-indole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 5-fluoro-1H-indole-3-carboxylate (500 mg, 2.125 mmol) and triethylamine (1721 mg, 17.00 mmol) in THF (5 ml) was added methanesulfonyl chloride (0.658 ml, 8.50 mmol). The mixture was stirred at RT for 2 h. The reaction mixture was then poured into water and extracted twice with Et2O. The organic extracts were combined, filtered through MgSO4, concentrated, and purified by column chromatography (SiO2; EtOAc/hex) to afford the title compound as a white solid.

Workup

  1. extractionextracted twice with Et2O
  2. filtrationfiltered through MgSO4
  3. concentrationconcentrated
  4. custompurified by column chromatography (SiO2; EtOAc/hex)

Sources & evidence

ORD record
ord-698277f5978a43599bbaff418bb9debe
Source dataset
uspto-grants-2016_04
Patent number
US09303045B2

Reaction notes

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