Triacetoxyperiodinane → HCID 67228195, compound

HRID 1515871Notes

Reaction equation

HRID 1515871 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[CH:21]([OH:28])[CH2:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]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][C:16]([O:19][CH3:20])=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:21](=[O:28])[CH2:22][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67228038HCID 67228038, compound

Product 1

HCID 67228195HCID 67228195, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(-benzenesulfonyl-6-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanol (1.39 g, 3.47 mmol) in dichloromethane (15 mL) was added Dess-Martin periodinane (5.15 g, 12.15 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, 18% ethyl acetate/hexanes) afforded 1-(-benzenesulfonyl-6-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-ethanone (0.59 g, 42%) as a light yellow solid: LC/MS m/e calcd for C21H22N2O4S [M+H]+ 399.48, observed 399.1.

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, 18% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-04c2aaaff233424b9311030e39949f5e
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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