Triacetoxyperiodinane → HCID 67229668, compound

HRID 1515931Notes

Reaction equation

HRID 1515931 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]1([S:29]([N:32]2[C:36]3=[N:37][CH:38]=[CH:39][CH:40]=[C:35]3[CH:34]=[C:33]2[CH:41]([OH:46])[CH2:42][CH:43]([CH3:45])[CH3:44])(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[C:23]1([S:29]([N:32]2[C:36]3=[N:37][CH:38]=[CH:39][CH:40]=[C:35]3[CH:34]=[C:33]2[C:41](=[O:46])[CH2:42][CH:43]([CH3:44])[CH3:45])(=[O:30])=[O:31])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67228631HCID 67228631, compound

Product 1

HCID 67229668HCID 67229668, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Dess-Martin periodinane reagent (3.3 g, 7.8 mmol) in dichloromethane (50 mL) at 25° C. was treated with 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-butan-1-ol (1.4 g, 4.1 mmol). The reaction was stirred at 25° C. for 3 h. At this time, the reaction was quenched by the addition of a saturated aqueous sodium bicarbonate solution. The resulting solution was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (20% ethyl acetate/petroleum ether) afforded 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-butan-1-one as a white solid (1.2 g, 82.1%): 1H NMR (300 MHz, d6-DMSO): δ ppm 8.54 (d, 1H, J=4.5 Hz), 8.27 (d, 2H, J=7.8 Hz), 8.17 (d, 1H, J=7.8 Hz), 7.76-7.66 (m, 3H), 7.58 (s, 1H), 7.42-7.38 (m, 1H), 2.91 (d, 2H, J=6.9 Hz), 2.23-2.18 (m, 1H), 1.01 (s, 3H), 0.99 (s, 3H).

Workup

  1. customAt this time, the reaction was quenched by the addition of a saturated aqueous sodium bicarbonate solution
  2. extractionThe resulting solution was extracted with ethyl acetate (3×100 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4af0a86c5cbf44fbb15bd2ebe43d85e1
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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