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

HRID 2080398Notes

Reaction equation

HRID 2080398 reaction equation
O1CCOCC1.Cl[C:8]1[CH:13]=[C:12]([CH:14]([S:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])[C:11]([Cl:31])=[CH:10][N:9]=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>C(OCC)(=O)C>[Cl:31][C:11]1[C:12]([CH:14]([S:23][C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])=[CH:13][C:8]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 312751,4-DioxaneHCID 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 8857Ethyl AcetateSolvent

Procedure

A 1,4-dioxane (1.0 ml) solution of the 2,5-dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (100 mg, 0.24 mmol) obtained in Example 54 and morpholine (200 μl) was stirred at 100° C. for 2 days under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (40 ml). The diluted mixture was washed with water and brine, dried and then concentrated under reduced pressure to give a residue. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to give the title compound (100 mg, 89%) as an oil.

Workup

  1. washThe diluted mixture was washed with water and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-9ee5c21a52fc454083722ca80d108027
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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