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Dichloromethane → 1-benzenesulfonyl-2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine

HRID 1432209
Notes
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Reaction equation

HRID 1432209 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:21]2[O:22][CH:23]=[CH:24][N:25]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:26].[OH2:27].O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[Mg+2].ClCCl.C(=O)([O-])O.[Na+]>CO>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19]([CH3:20])(=[O:27])=[O:26])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:21]2[O:22][CH:23]=[CH:24][N:25]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)HCID 225044351-benzenesulfonyl-2-(oxazol-2-yl)-5-methylthio-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 225043901-benzenesulfonyl-2-(oxazol-2-yl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine
Yield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-benzenesulfonyl-2-(oxazol-2-yl)-5-methylthio-1H-pyrrolo[2,3-b]pyridine (28 mg), magnesium monoperoxyphtalate hexahydrate (116 mg, 80% purity), dichloromethane (1.2 ml) and methanol (0.5 ml) was stirred at 0° C. for 30 minutes. To the reaction mixture was added a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with dichloromethane, washed with a saturated aqueous NaCl solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:3) to obtain 14 mg of the desired product.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washwashed with a saturated aqueous NaCl solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-482322985f6c41b5805d43b1ab1b70b5
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07612070B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes