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

HRID 1515922Notes

Reaction equation

HRID 1515922 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:20]([OH:27])[CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]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>ClCCl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:20](=[O:27])[CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 672290511-(1-benzenesulfonyl-5-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol

Product 1

HCID 672293961-(1-benzenesulfonyl-5-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanoneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(1-benzenesulfonyl-5-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol (3.13 g, 8.15 mmol) in dichloromethane (150 ml) was added Dess-Martin periodinane (5.18 g, 12.2 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 (40 mL). The mixture was extracted with ethyl acetate (200 mL), washed with a saturated aqueous sodium bicarbonate solution (40 mL×3), 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, 60% dichloromethane/hexanes) to afford 1-(1-benzenesulfonyl-5-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone (2.8 g, 90%) as a light yellow solid: LC/MS m/e calcd for C21H22N2O3S [M+H]+ 383.49, observed 382.8.

Workup

  1. customquenched with a saturated aqueous sodium bicarbonate solution (40 mL)
  2. extractionThe mixture was extracted with ethyl acetate (200 mL)
  3. washwashed with a saturated aqueous sodium bicarbonate solution (40 mL×3), 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, 60% dichloromethane/hexanes)

Sources & evidence

ORD record
ord-1a4f3c5eec5c4cbebe3350556a49e881
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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