Water → 1-benzenesulfonyl-2-methyl-4-trifluoromethyl-1H-indole

HRID 2101922Notes

Reaction equation

HRID 2101922 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][CH2:24]CCC.CI.O>C1COCC1>[CH3:24][C:11]1[N:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])[C:18]2[C:13]([CH:12]=1)=[C:14]([C:19]([F:21])([F:22])[F:20])[CH:15]=[CH:16][CH:17]=2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 578003941-benzenesulfonyl-4-trifluoromethyl-1H-indoleHCID 178418339Butyllithium

Product 1

HCID 578003011-benzenesulfonyl-2-methyl-4-trifluoromethyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(phenylsulfonyl)-4-(trifluoromethyl)-1H-indole (60.0 g, 184.6 mmol) in THF (300 mL) at 0° C. was added n-BuLi (88.6 mL of a 2.50 M solution in hexanes), dropwise over 5 min. The mixture was stirred 1 h and methyl iodide (23.0 mL, 369.2 mmol) was added dropwise over 5 min. The mixture was stirred at 0° C. for 2.5 h and then overnight, slowly warming to rt, poured into water and extracted with Et2O (×3). Combined organics were washed (H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 26.0 g of the title compound as a colorless oil: MS (ES) m/z 338 (M−1).

Workup

  1. stirringThe mixture was stirred at 0° C. for 2.5 h
  2. extractionextracted with Et2O (×3)
  3. washCombined organics were washed (H2O, brine)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-8a8622998e7343fd86b2ff72ba9054f3
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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