Triacetoxyperiodinane → [1-benzenesulfonyl-2-(2-cyclopentyl-acetyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-carbamic acid tert-butyl ester

HRID 1515850Notes

Reaction equation

HRID 1515850 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([CH:17]([OH:24])[CH2:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[N:14]([S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:11]2=[N:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:9]=[C:10]2[CH:16]=[C:15]([C:17](=[O:24])[CH2:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[N:14]([S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[C:11]2=[N:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67229605HCID 67229605, compound

Product 1

HCID 67227791[1-benzenesulfonyl-2-(2-cyclopentyl-acetyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-carbamic acid tert-butyl esterYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of [1-benzenesulfonyl-2-(2-cyclopentyl-1-hydroxy-ethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-carbamic acid tert-butyl ester (0.57 g, 1.18 mmol) in dichloromethane (10 mL) was added a solution of Dess-Martin periodinane in dichloromethane (0.3 M, 7.87 mL, 2.36 mmol) at 25° C. The mixture was stirred at 25° C. for 1 h and then quenched with a saturated aqueous sodium bicarbonate solution (20 mL). The mixture was extracted with ethyl acetate (100 mL), washed with a saturated aqueous sodium bicarbonate solution (3×20 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, 25% ethyl acetate/hexanes) afforded [1-benzenesulfonyl-2-(2-cyclopentyl-acetyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-carbamic acid tert-butyl ester (0.375 g, 66%) as a light yellow solid: LC/MS m/e calcd for C25H29N3O5S [M+H]+ 484.59, observed 484.2.

Workup

  1. customquenched with a saturated aqueous sodium bicarbonate solution (20 mL)
  2. extractionThe mixture was extracted with ethyl acetate (100 mL)
  3. washwashed with a saturated aqueous sodium bicarbonate solution (3×20 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, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9864b2ad69c9404289ced52dbebe7240
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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