m-Chloroperbenzoic acid → 2,3-Dimethyl-5-methylsulfinyl-7-phenacylpyrrolo[2,3-b]pyridine

HRID 1756073Notes

Reaction equation

HRID 1756073 reaction equation
[CH3:1][C:2]1[N:21]=[C:5]2[N:6]([CH2:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:14])[CH:7]=[C:8]([S:10][CH3:11])[CH:9]=[C:4]2[C:3]=1[CH3:22].C1C=C(Cl)C=C(C(OO)=[O:31])C=1>C(Cl)Cl>[CH3:1][C:2]1[N:21]=[C:5]2[N:6]([CH2:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:14])[CH:7]=[C:8]([S:10]([CH3:11])=[O:31])[CH:9]=[C:4]2[C:3]=1[CH3:22]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 199167972,3-Dimethyl-5-methylthio-7-phenacylpyrrolo[2,3-b]pyridine

Product 1

HCID 217438492,3-Dimethyl-5-methylsulfinyl-7-phenacylpyrrolo[2,3-b]pyridineYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3-dimethyl-5-methylthio-7-phenacylpyrrolo[2,3-b]pyridine (35 mg, 0.1 mmol) in 20 ml CH2Cl2 was cooled to -20° C. an treated with 71% m-CPBA (27 mg, 0.1 mmol) for 30 min. The volume was adjusted 50 ml with CH2Cl2 and the organic layer washed twice with 50 ml 5% Na2CO3 and once with 2M HCl (reextraction trice with 25 ml CH2Cl2). The organic layer was dried over MgSO4 and evaporated leaving 15 mg (41%) pure title compound.

Workup

  1. washthe organic layer washed twice with 50 ml 5% Na2CO3 and once with 2M HCl (reextraction trice with 25 ml CH2Cl2)
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-4b5569d40c9843ca825cbcdc092976bd
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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