Triacetoxyperiodinane → 1-(1-benzenesulfonyl-5-ethanesulfinyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone

HRID 1515904Notes

Reaction equation

HRID 1515904 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19][CH2:20][CH3:21])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:22]([OH:29])[CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:32]>ClCCl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19]([CH2:20][CH3:21])=[O:32])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:22](=[O:29])[CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 672276411-(1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol

Product 1

HCID 672282151-(1-benzenesulfonyl-5-ethanesulfinyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanoneYield 48.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(1-benzenesulfonyl-5-ethylsulfanyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol (3.0 g, 7.0 mmol) in dichloromethane (150 mL) was added Dess-Martin periodinane (7.4 g, 17.4 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 1 h and then quenched with a saturated aqueous sodium bicarbonate solution (60 mL). The mixture was extracted with ethyl acetate (250 mL), washed with a saturated aqueous sodium bicarbonate solution (3×50 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 20% ethyl acetate/hexanes) to afford 1-(1-benzenesulfonyl-5-ethanesulfinyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone (1.5 g, 48%) as a light yellow solid: LC/MS m/e calcd for C22H24N2O4S2 [M+H]+ 445.58, observed 444.9.

Workup

  1. customquenched with a saturated aqueous sodium bicarbonate solution (60 mL)
  2. extractionThe mixture was extracted with ethyl acetate (250 mL)
  3. washwashed with a saturated aqueous sodium bicarbonate solution (3×50 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-885dd9b2c0ca44bdbef03371e0dfb03d
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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