Ethyl Acetate → 2-(2-Ethanesulfonyl-1-hydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile

HRID 646582Notes

Reaction equation

HRID 646582 reaction equation
C(S[CH2:4][C:5]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([C:17]#[N:18])=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:11]=2)([OH:7])[CH3:6])C.C(=O)(O)[O-].[Na+].[OH:28][O:29][S:30]([O-:32])=[O:31].[K+:33].[C:34](OCC)(=O)[CH3:35]>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[OH:28][O:29][S:30]([O-:32])=[O:31].[K+:33].[CH2:34]([S:30]([CH2:6][C:5]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([C:17]#[N:18])=[C:12]([C:19]([F:22])([F:20])[F:21])[CH:11]=2)([OH:7])[CH3:4])(=[O:32])=[O:29])[CH3:35]

Participants

7

Reactant 4

HCID 8857Ethyl Acetate3×HCID 516892Sodium BicarbonateHCID 117096572-(2-Ethylsulfanyl-1-hydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrileHCID 23707502Potassium hydroxy sulfite

Product 2

HCID 115522382-(2-Ethanesulfonyl-1-hydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrileHCID 23707502Potassium hydroxy sulfite

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

The (−) enantiomer of 2-(2-ethylsulfanyl-1-hydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile, the compound prepared as in Example 86 above (1 equivalent) was dissolved in ethyl acetate (5 mL/mmol). A separate aqueous solution of OXONE® (3 equivalents) and Bu4NHSO4 (0.3 mol %) (10 mL water/g of OXONE®) was prepared and the pH of this solution adjusted to about 7 by the addition of saturated sodium bicarbonate solution. After the pH adjustment, this aqueous solution was added to the ethyl acetate solution and the resulting biphasic mixture vigorously stirred. After 8 hours, an additional 3 equivalents of the pH-adjusted OXONE® solution was added and the mixture stirred overnight. Ethyl acetate (10 mL/mmol of sulfide) was added and the aqueous phase was removed. The organic phase was washed with brine, dried over anhydrous Na2SO4, concentrated to yield a yellow solid. This crude material (yellow solid) was purified using column chromatography (silica gel, ethyl acetate as eluent) to yield the title compound as a pale yellow solid.

Workup

  1. stirringthe mixture stirred overnight
  2. customthe aqueous phase was removed
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto yield a yellow solid
  7. customThis crude material (yellow solid) was purified

Sources & evidence

ORD record
ord-268cd4e0ac814950b6f98027760ae379
Source dataset
uspto-grants-2010_04
Patent number
US07705147B2

Reaction notes

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