Ethanol → 2-Methyl-1'H,2H-3,4'-bipyrazole

HRID 238370Notes

Reaction equation

I[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.C(OC([N:15]1[CH:19]=[C:18](B(O)O)[CH:17]=[N:16]1)=O)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1>[CH3:7][N:6]1[C:2]([C:18]2[CH:19]=[N:15][NH:16][CH:17]=2)=[CH:3][CH:4]=[N:5]1

Participants

Conditions

Temperature: 100 °C

Procedure

Under a nitrogen atmosphere, a mixture of 5-iodo-1-methyl-1H-pyrazole (750 mg), [1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl]boronic acid (1.27 g), tetrakis(triphenylphosphine)palladium(0) (209 mg), 2 M sodium carbonate aqueous solution (3.6 mL), ethanol (3.6 mL) and toluene (7.2 mL) was stirred at 100° C. for 14 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=4:1 to 0:10), so as to obtain the title compound (176 mg) in the form of a light yellow solid.

Workup

extractionthe obtained mixture was then extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationwas then concentrated under a reduced pressure
customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=4:1 to 0:10)

Sources & evidence

ORD record: ord-a540602f3ca5468981ff4c7803c95013
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642626B2

Reaction notes

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