Acetonitrile → ethyl 1-(3,5-dichloropyridin-2-yl)-3-(prop-2-ynyloxy)-1H-pyrazole-5-carboxylate

HRID 453078Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][C:11]([OH:19])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C(#N)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]#[CH:32]>O>[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][C:11]([O:19][CH2:32][C:31]#[CH:30])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a 100 mL flask, ethyl 1-(3,5-dichloropyridin-2-yl)-3-hydroxy-1H-pyrazole-5-carboxylate (0.7 g, 2.32 mmol), acetonitrile (10 mL), potassium carbonate (0.32 g, 2.32 mmol) and 3-bromoprop-1-yne (0.27 g, 2.32 mmol) were added sequentially. The reaction mixture was heated to 60° C. for 2 hours. Then the reaction mixture was poured into water (100 mL), extracted with ethyl acetate (2×100 mL). The organic layer was washed with saturated sodium carbonate solution (80 mL) and saturated brine (80 mL), dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the compound (0.30 g) as yellow oil in 38% yield.

Workup

extractionextracted with ethyl acetate (2×100 mL)
washThe organic layer was washed with saturated sodium carbonate solution (80 mL) and saturated brine (80 mL)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-048feca8194049d9a6c554334717bf96
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492409B2

Reaction notes

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