Hexane → HCID 178439461, compound

HRID 1926808Notes

Reaction equation

HRID 1926808 reaction equation
[CH2:1]([CH:4]1[CH2:8][N:7]([CH2:9][C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[C:6](=[O:19])[CH2:5]1)[CH2:2][CH3:3].ClC1C=C(C=CC=1)C(OO)=[O:25].CCCCCC>COCCOC>[O-:25][N+:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:10]([CH2:9][N:7]3[CH2:8][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][C:6]3=[O:19])=[CH:11][NH:12][C:13]=12

Participants

5

Reactant 3

HCID 8058HexaneHCID 70297m-Chloroperbenzoic acidHCID 577430754-propyl-1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrrolidin-2-one

Product 1

HCID 178439461HCID 178439461, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To 4-propyl-1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrrolidin-2-one 231 (100 mg, 1 eq, 0.39 mmol) dissolved in 1,2-dimethoxyethane (3 ml) is added m-chloroperoxybenzoic acid (111 mg, 1.6 eq, 0.64 mmol). The resulting solution is stirred at room temperature for 20 hours. Hexane (10 ml) is added to the reaction mixture, and the decanted syrup is washed twice with hexane by decantation and dried under vacuum. To the residual solid are added 3 ml of water and a saturated solution of K2CO3 until pH 9. The resulting mixture is extracted with CH2Cl2 and the organic phase is dried over MgSO4. Volatiles are removed under reduced pressure and the residue is purified twice by chromatography on silicagel (CH2Cl2/MeOH/NH4OH 95/5/05) to give 50 mg of 1-[(7-oxido-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl]-4-propylpyrrolidin-2-one 239.

Workup

  1. washthe decanted syrup is washed twice with hexane by decantation
  2. customdried under vacuum
  3. additionTo the residual solid are added 3 ml of water
  4. extractionThe resulting mixture is extracted with CH2Cl2
  5. dry with materialthe organic phase is dried over MgSO4
  6. customVolatiles are removed under reduced pressure
  7. customthe residue is purified twice by chromatography on silicagel (CH2Cl2/MeOH/NH4OH 95/5/05)

Sources & evidence

ORD record
ord-08d566ab8b8a4e8c870099f90f442b9f
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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