m-Chloroperbenzoic acid → HCID 178507661, compound

HRID 1623910Notes

Reaction equation

HRID 1623910 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:17])C=1>C(Cl)Cl.CO>[NH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N+:6]=1[O-:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 178507661HCID 178507661, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of 5-fluoropyridin-2-amine (500 mg, 4.46 mmol) in DCM/MeOH (20 mL) in an ice-bath was added MCPBA (1199 mg, 5.35 mmol). The reaction was slowly warmed to room temperature and stirred overnight. The red-orange color solution was loaded to a SCX resin, which was then washed with methanol, eluted with 2 N ammonia in methanol to collect the product. Evaporation of the solvent gave the title compound as yellow-brownish solid (420 mg) without further purification. LCMS m/z=129.2 [M+H]+.

Workup

  1. washwas then washed with methanol
  2. washeluted with 2 N ammonia in methanol
  3. customto collect the product
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f4916bbd27de4713972e39d8150f9d7a
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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