Morpholine → 4-[5-Chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridin-2-yl]morpholine

HRID 748841Notes

Reaction equation

HRID 748841 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]([S:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[F:16])[C:5]([Cl:25])=[CH:4][N:3]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>O1CCOCC1>[Cl:25][C:5]1[C:6]([CH:8]([S:17][C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[F:16])=[CH:7][C:2]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 231145672,5-Dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine

Product 1

HCID 231147414-[5-Chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridin-2-yl]morpholineYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the 2,5-dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (100 mg, 0.24 mmol) obtained in Example 342 and morpholine (200 μl) in 1,4-dioxane (1.0 ml) was stirred under nitrogen atmosphere at 100° C. for 2 days. The reaction mixture was cooled to room temperature. After dilution with ethyl acetate (40 ml), the solution was washed with water and brine, dried and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to yield the title compound (100 mg, 89%) as an oil.

Workup

  1. washAfter dilution with ethyl acetate (40 ml), the solution was washed with water and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-f5c1236370e24b3188a3ad9f583b6be2
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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