m-Chloroperbenzoic acid → HCID 178524356, compound

HRID 2365427Notes

Reaction equation

HRID 2365427 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[N:11][NH:10][C:9]=2[C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[CH:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([C:29]([O:31]O)=[O:30])[CH:23]=1>CCOC(C)=O>[Cl:28][C:26]1[CH:25]=[C:24]([CH:23]=[CH:22][CH:27]=1)[C:29]([OH:31])=[O:30].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[N:11][NH:10][C:9]=2[C:13]2[C:21]3[C:16](=[N+:17]([O-:30])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 136159640HCID 136159640, compound

Product 1

HCID 178524356HCID 178524356, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-[4-(3-chlorophenyl)-2H-pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (147 mg, 0.5 mmol) in EtOAc (5 mL) was cooled in an ice bath and m-CPBA (148 mg, 0.6 mmol) added in one portion. The resulting suspension was stirred at 0° C. for 3 hours. After this time a second portion of m-CPBA (62 mg, 0.25 mmol) was added and the reaction stirred for an additional 14 hours, during which time the reaction warmed to room temperature. The reaction mixture was then filtered and the solids washed with ethyl acetate (2 mL) and air dried on the pump. This afforded 3-[4-(3-chlorophenyl)-2H-pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine 7-oxide meta-chlorobenzoate salt as white solid in 67% yield.

Workup

  1. stirringthe reaction stirred for an additional 14 hours, during which time the reaction
  2. temperaturewarmed to room temperature
  3. filtrationThe reaction mixture was then filtered
  4. washthe solids washed with ethyl acetate (2 mL) and air
  5. customdried on the pump

Sources & evidence

ORD record
ord-37262a9cf09a46bb82b5d102dc3417c3
Source dataset
uspto-grants-2014_04
Patent number
US08697697B2

Reaction notes

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