m-Chloroperbenzoic acid → HCID 23114642, compound

HRID 748840Notes

Reaction equation

HRID 748840 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[CH:19]([S:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[F:27]>C(Cl)Cl.CCOCC>[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[CH:19]([S:28]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)=[O:9])[C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[F:27]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 231146243-Chloro-4-{[(4-chlorophenyl)sulfanyl](2,5-difluorophenyl)methyl}pyridine

Product 1

HCID 23114642HCID 23114642, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

After 3-chloroperbenzoic acid (33 mg, 0.20 mmol) was added to a solution of the 3-chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (75 mg, 0.20 mmol), which had been obtained in Example 341, in methylene chloride (10 ml), the mixture was stirred for 3 hours under ice cooling. The reaction mixture was diluted with ether (80 ml). The solution was washed with water and brine, and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1), whereby the title compound (48 mg, 60%) was obtained as a diastereomeric mixture (1:1).

Workup

  1. washThe solution was washed with water and brine
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1), whereby the title compound (48 mg, 60%)
  4. customwas obtained as a diastereomeric mixture (1:1)

Sources & evidence

ORD record
ord-d5407bbb3da5464c8266cf9612e48d80
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

Loading…