Dichloromethane → HCID 67228345, compound

HRID 1515617Notes

Reaction equation

HRID 1515617 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:21]([OH:29])[CH2:22][CH:23]2[CH2:28][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][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:21](=[O:29])[CH2:22][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 67228832HCID 67228832, compound

Product 1

HCID 67228345HCID 67228345, compoundYield 100.3%

Conditions

Temperature
25 °C

Procedure

To a 250 mL round bottomed flask charged with 1-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclohexyl-ethanol (240 mg, 0.58 mmol) was added a solution of Dess-Martin periodinane in dichloromethane (0.3 M, 3.86 mL, 1.16 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 to give 1-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclohexyl-ethanone (240 mg, quant.) as a light yellow solid which was used in the next step without further purification: LC/MS m/e calcd for C22H24N2O4S [M+H]+ 413.51, observed 413.1.

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

Sources & evidence

ORD record
ord-131527cf38e748bfb698f2fdd020de5d
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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