m-Chloroperbenzoic acid → HCID 178526231, compound

HRID 1506204Notes

Reaction equation

HRID 1506204 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[C:15]2[CH:21]=[CH:20][NH:19][C:16]2=[N:17][CH:18]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Br:12][C:13]1[CH:14]=[C:15]2[CH:21]=[CH:20][NH:19][C:16]2=[N+:17]([O-:9])[CH:18]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178526231HCID 178526231, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

m-Chloroperbenzoic acid (25 wt % water content, 322 mg, 1.40 mmol) in ethyl acetate (5 mL) was gradually added dropwise to 5-bromo-1H-pyrrolo[2,3-b]pyridine (184 mg, 0.934 mmol) in ethyl acetate (10 mL), and the reaction mixture was stirred at room temperature for 6 hours. After addition of saturated aqueous sodium hydrogen carbonate, the reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was mixed with a mixture of ethyl acetate/hexane=1/1 (v/v), and the solid was collected by filtration, washed with hexane and dried under reduced pressure to give the title compound as a light brown solid (150 mg, yield 75%).

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was mixed with a mixture of ethyl acetate/hexane=1/1 (v/v)
  5. filtrationthe solid was collected by filtration
  6. washwashed with hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-8aef1c7ce0404966914b68bd903ba596
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

Loading…