Methyl iodide → Ethyl 3-(3,4-difluorophenyl)-2-(methylsulfanyl)-3,4,5,6-tetrahydropyridine-3-carboxylate

HRID 71142Notes

Reaction equation

[CH3:1]I.[F:3][C:4]1[CH:5]=[C:6]([C:11]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:15][CH2:14][NH:13][C:12]2=[S:17])[CH:7]=[CH:8][C:9]=1[F:10]>C(#N)C.C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[C:6]([C:11]2([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:15][CH2:14][N:13]=[C:12]2[S:17][CH3:1])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl iodide (0.520 mL) was added to a mixture of ethyl 3-(3,4-difluorophenyl)-2-thioxopiperidine-3-carboxylate (500 mg) in acetonitrile (5 mL) at room temperature, and the mixture was stirred at 50° C. for 3 hr. The reaction mixture was diluted with ethyl acetate, the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (530 mg).

Workup

washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-b20871ed5cfa458ba76516d068b67645
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822699B2

Reaction notes

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