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

HRID 2101921Notes

Reaction equation

HRID 2101921 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:14]1([S:20]([N:7]2[C:8]3[C:4](=[C:3]([C:2]([F:1])([F:12])[F:13])[CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 198037034-(Trifluoromethyl)-1H-indole

Product 1

HCID 578003941-benzenesulfonyl-4-trifluoromethyl-1H-indoleYield 82%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-(trifluoromethyl)-1H-indole (0.535 g, 2.89 mmol; step A above), tetrabutylammonium bromide (0.097 g, 0.30 mmol) and benzenesulfonyl chloride (0.44 mL, 3.5 mmol) in PhMe (5 mL) at rt was added 50 wt % NaOH (3 mL) and H2O (2 mL). The mixture was stirred 30 min, partitioned between Et2O/H2O and the layers were separated. The organic layer was washed (H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.771 g of the title compound as a thick, pale yellow oil: 1H NMR (300 MHz, methanol-d4) δ 8.25 (d, J=8.3 Hz, 1H), 8.00-7.94 (m, 2H), 7.88 (d, J=3.8 Hz, 1H), 7.65-7.58 (m, 1H), 7.57-7.41 (m, 4H), 6.87 (br. s, 1H).

Workup

  1. custompartitioned between Et2O/H2O
  2. customthe layers were separated
  3. washThe organic layer was 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-6e6a1f5ad1a94ce48ab1b14b0e15f643
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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