m-Chloroperbenzoic acid → HCID 178493206, compound

HRID 505388Notes

Reaction equation

HRID 505388 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][S:10][C:11]2[NH:26][C:14]3=[N:15][C:16]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[C:17]([CH3:19])[CH:18]=[C:13]3[N:12]=2)[C:4]=1[CH3:27].ClC1C=CC=C(C(OO)=[O:36])C=1.C(=O)(O)[O-].[Na+]>CO.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][S:10]([C:11]2[NH:26][C:14]3=[N:15][C:16]([O:20][CH2:21][C:22]([F:23])([F:24])[F:25])=[C:17]([CH3:19])[CH:18]=[C:13]3[N:12]=2)=[O:36])[C:4]=1[CH3:27]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 178493197HCID 178493197, compound

Product 1

HCID 178493206HCID 178493206, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent2×

Procedure

2-(((4-Methoxy-3-methyl-2-pyridinyl)methyl)thio)-6-methyl-5-(2,2,2-trifluoroethoxy)-3H-imidazo[4,5-b]pyridine (270 mg, 0.68 mmol) was dissolved in a mixture of methanol (2 ml) and toluene (18 ml), and a solution of metachloroperbenzoic acid (162 mg) in a mixture of methanol (0.5 ml) of toluene (0.5 ml) were added dropwise at −40° C. under nitrogen flow. After stirred at −20° C. to −40° C. for 2 hours, a sodium bicarbonate solution was added, the mixture was extracted with chloroform (30 ml), and dried over sodium sulfate. The solvent was evaporated, and the solid was precipitated from a mixture of chloroform and n-hexane to yield the title compound (263 mg, 0.63 mmol, 93%) as a purple gray solid.

Workup

  1. additionwere added dropwise at −40° C. under nitrogen flow
  2. extractionthe mixture was extracted with chloroform (30 ml)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe solid was precipitated from a mixture of chloroform and n-hexane

Sources & evidence

ORD record
ord-6d0d1146482a438d95521c61603625c9
Source dataset
uspto-grants-2010_08
Patent number
US07781452B2

Reaction notes

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