m-Chloroperbenzoic acid → HCID 178526273, compound

HRID 1622890Notes

Reaction equation

HRID 1622890 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:16]>CCOCC>[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N+:6]([O-:16])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 207844625-Fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 178526273HCID 178526273, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred solution of 5-fluoro-1H-pyrrolo[2,3-b]pyridine (5.00 g, 36.73 mmol) in Et2O (120 mL), under a nitrogen atmosphere, is added 3-chloroperoxybenzoic acid (11.09 g, 64.28 mmol) portionwise over 5 minutes and the reaction stirred for 3 h. The reaction is then cooled to 5° C., filtered and the solid washed with Et2O (ca. 100 mL). This is dried in vacuo to give the title compound as a pale green crystalline solid (4.317 g, 28.38 mmol). MS (m/z): 153 (M+1).

Workup

  1. filtrationfiltered
  2. washthe solid washed with Et2O (ca. 100 mL)
  3. customThis is dried in vacuo

Sources & evidence

ORD record
ord-cd56f2b3772149bda088090389b0c8aa
Source dataset
uspto-grants-2014_07
Patent number
US08778946B2

Reaction notes

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