Ethanol → 1'-(4-Fluorophenyl)-2-methyl-1'H,2H-3,4'-bipyrazole

HRID 238372Notes

Reaction equation

HRID 238372 reaction equation
I[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18](B(O)O)[CH:17]=[N:16]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O.C1(C)C=CC=CC=1>[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18]([C:2]3[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=3)[CH:17]=[N:16]2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 133340655-Iodo-1-methyl-1H-pyrazoleHCID 467386841-(4-Fluorophenyl)pyrazole-4-boronic acid

Product 1

HCID 866848711'-(4-Fluorophenyl)-2-methyl-1'H,2H-3,4'-bipyrazoleYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Under a nitrogen atmosphere, a mixture of 5-iodo-1-methyl-1H-pyrazole (600 mg), [1-(4-fluorophenyl)-1H-pyrazol-4-yl]boronic acid (650 mg), tetrakistriphenylphosphine palladium (166 mg), 2 M sodium carbonate aqueous solution (2.9 mL), ethanol (3.0 mL) and toluene (6.0 mL) was stirred at 100° C. for 4 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was concentrated under a reduced pressure, and the residue was then purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to ethyl acetate), so as to obtain the title compound (450 mg) in the form of a light yellow solid.

Workup

  1. extractionthe obtained mixture was then extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under a reduced pressure
  3. customthe residue was then purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to ethyl acetate)

Sources & evidence

ORD record
ord-ffefd9914333427893e53e9a6ac5a748
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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