m-Chloroperbenzoic acid → 3-(tert-butyl-5-fluoro-6-(methylsulfinyl)pyrimidin-2-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridine

HRID 526981Notes

Reaction equation

HRID 526981 reaction equation
[C:1]([C:5]1[C:10]([F:11])=[C:9]([S:12][CH3:13])[N:8]=[C:7]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[NH:16][CH:15]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:32])C=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([C:5]1[C:10]([F:11])=[C:9]([S:12]([CH3:13])=[O:32])[N:8]=[C:7]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[NH:16][CH:15]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 672859433-(tert-butyl-5-fluoro-6-(methylthio)pyrimidin-2-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridine2×

Product 1

HCID 672858693-(tert-butyl-5-fluoro-6-(methylsulfinyl)pyrimidin-2-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To the solution of 3-(tert-butyl-5-fluoro-6-(methylthio)pyrimidin-2-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridine, 40b, (0.05 g, 0.11 mmol) in CH2Cl2 (3.4 mL) was added mCPBA (0.02 g, 0.11 mmol). The reaction mixture was stirred for 1 h. The reaction mixture was diluted with CH2Cl2 (10 mL) and saturated NaHCO3 solution (5 mL). The aqueous layer was extracted with CH2Cl2 (10 mL). The combined organic phases were washed again with aqueous saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated in vacuo to afford the desired product that was used without further purification.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2 (10 mL)
  2. washThe combined organic phases were washed again with aqueous saturated NaHCO3 solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa71561232804b2ab929ef42d3881d03
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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