Dimethylformamide → 5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile

HRID 534102

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=2[CH3:16])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25].CN(C=O)C.[H-].[Na+]>O>[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=2[CH3:16])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A flask was charged with 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (27.77 g, 90.41 mmol), pyridine-2-thiol (10.55 g, 94.93 mmol), and DMF (300 mL). The reaction was cooled to 0° C. and 95% sodium hydride (2.741 g, 108.5 mmol) was added portionwise. The reaction was stirred at ambient temperature overnight, then carefully diluted with water (2 L) and extracted with ethyl acetate. The organic layer was washed with brine (4×500 mL), dried over sodium sulfate and concentrated to afford 5-(pyridin-2-ylthio)-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (29.50 g, 87.43 mmol, 96.70% yield) as yellow solid.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with brine (4×500 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-f3be4bd4c6104e7fa6e03fbe14fbfe17
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853409B2

Linked notes

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