Dimethylformamide → 1-Methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}-1H-pyrazole

HRID 238360Notes

Reaction equation

I[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)#[CH:9].C(N(CC)CC)C.CN(C)C=O>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:7][N:6]1[C:2]([C:9]#[C:8][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=2)=[CH:3][CH:4]=[N:5]1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 5-iodo-1-methyl-1H-pyrazole (8.00 g), 1-ethynyl-4-(trifluoromethyl)benzene (6.54 g), copper(I) iodide (110 mg), bis(triphenylphosphine)palladium(II) dichloride (1.35 g), triphenylphosphine (504 mg), triethylamine (8.00 mL) and dimethylformamide (70 mL) was stirred at 75° C. for 2 hours. Thereafter, the reaction solution was added to water, and the obtained mixture was then extracted with ethyl acetate. The organic layer was successively washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=85:15 to 75:25), so as to obtain the title compound (7.74 g) in the form of a yellow solid.

Workup

extractionthe obtained mixture was then extracted with ethyl acetate
washThe organic layer was successively washed with water
dry with materiala saturated saline, and was then dried over anhydrous magnesium sulfate
concentrationfollowed by vacuum concentration
customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=85:15 to 75:25)

Sources & evidence

ORD record: ord-2746452428f0474e8b37d0e24d47a569
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642626B2

Reaction notes

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