Ethyl Acetate → 3-(6-methoxy-2-(methylsulfonyl)pyrimidin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 68332Notes

Reaction equation

HRID 68332 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7](SC)[N:6]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:12]=2)[CH:4]=1.OO[S:31]([O-:33])=[O:32].[K+].[C:35](OCC)(=O)C>>[CH3:1][O:2][C:3]1[N:8]=[C:7]([S:31]([CH3:35])(=[O:33])=[O:32])[N:6]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:21])=[O:22])[CH:12]=2)[CH:4]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 23707502Potassium hydroxy sulfiteHCID 668890553-(6-methoxy-2-(methylthio)pyrimidin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 668887123-(6-methoxy-2-(methylsulfonyl)pyrimidin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Procedure

A mixture of EXAMPLE 1A (6.2 g, 15.0 mmol) and OXONE® (92 g, 150 mmol) in ethyl acetate (350 mL) was stirred at 77° C. for 2 days. The mixture was filtered and the solids were washed with dichloromethane and concentrated to give the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solids were washed with dichloromethane
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0360c4391493435bbe96cde5a3e8473a
Source dataset
uspto-grants-2014_09
Patent number
US08822446B2

Reaction notes

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