Dimethylformamide → 2-{[(4-Chlorophenyl)sulfanyl](2,5-difluorophenyl)methyl}-3-methylpyridine

HRID 748744Notes

Reaction equation

CN(C)C=O.Cl.Cl[CH:8]([C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[F:23])[C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][N:10]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31][CH:8]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a dimethylformamide (5 ml) solution of the 2-[chloro-(2,5-difluorophenyl)methyl]-3-methylpyridine hydrochloride (94 mg, 0.32 mmol) obtained in Referential Example 14 were added 4-chlorobenzenethiol (70 mg, 0.49 mmol) and potassium carbonate (265 mg, 1.92 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at 50° C. for 1 hour. After cooling to room temperature, diethyl ether (50 ml) was added to the reaction mixture. The resulting mixture was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (hexane:ethyl acetate 10:1), whereby the title compound (103 mg, 89%) was obtained as an oil.

Workup

temperatureAfter cooling to room temperature
washThe resulting mixture was washed with water and brine
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customwas obtained as an oil

Sources & evidence

ORD record: ord-4a0a63c62b6e4423ad675019fdde69ee
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399775B2

Reaction notes

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