Dimethylformamide → 2,5-Dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine

The 2,5-dichloro-4-[(2,5-difluorophenyl)-hydroxymethyl]pyridine (580 mg, 2.0 mmol) obtained in Referential Example 24 was dissolved in thionyl chloride (3.0 ml). To the resulting solution was added a catalytic amount of dimethylformamide. The resulting mixture was stirred for 17 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added toluene, followed by further concentration. The residue was dissolved in dimethylformamide (10 ml). To the resulting solution were added 4-chlorobenzenethiol (375 mg, 2.6 mmol) and potassium carbonate (414 mg, 3 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at 50° C. for 17 hours. After the reaction mixture was cooled to room temperature, diethyl ether (60 ml) was added thereto. The resulting mixture was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel chromatography (hexane:ether=10:1) to give the title compound (484 mg, 58%) as a solid.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionTo the residue was added toluene
3. concentrationfollowed by further concentration
4. dissolutionThe residue was dissolved in dimethylformamide (10 ml)
5. stirringThe resulting mixture was stirred at 50° C. for 17 hours
6. washThe resulting mixture was washed with water and brine
7. dry with materialThe organic layer was dried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue thus obtained

ORD record

ord-32bf6e7f1ab34507a881471077a01534

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932271B2