Dichloromethane → HCID 67228998, compound
Reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[CH:19]([OH:26])[CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]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.C(Cl)Cl>>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19](=[O:26])[CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Conditions
- Temperature
- 25 °C
Procedure
To a 250 mL round bottomed flask charged with 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanol (690 mg, 1.86 mmol) was added a 0.3 M solution of Dess-Martin periodinane in methylene chloride (12.4 mL, 3.72 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 1 h before quenching with saturated aqueous sodium bicarbonate solution (60 mL). The mixture was extracted with ethyl acetate (250 mL), washed with saturated aqueous sodium bicarbonate solution (50 mL×3), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to give 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-ethanone (685 mg, quant.) as a light yellow solid which was used for the next step without further purification: LC/MS m/e calcd for C20H21N2O3S [M+H]+ 369.12, observed 369.0.
Workup
- custombefore quenching with saturated aqueous sodium bicarbonate solution (60 mL)
- extractionThe mixture was extracted with ethyl acetate (250 mL)
- washwashed with saturated aqueous sodium bicarbonate solution (50 mL×3), brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-32d4fd805dd64f4ca951febda561a49d
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222416B2
Reaction notes
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