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

HRID 2088994Notes

Reaction equation

HRID 2088994 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]pyridineYield 94%

Procedure

A mixture of Example 49a (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 reaction mixture was filtered and the solids were washed with dichloromethane. The organic phase was concentrated in vacuo to give the title compound (6.3 g, 14.2 mmol, 94% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids were washed with dichloromethane
  3. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-aff8ee7bcc134955bf434f81d07c373b
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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