Reaction #1099046

Reaction equation

1-(3-bromo-phenyl)-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester

(E)-2-(4-chlorophenyl)vinyl boronic acid

potassium phosphate

→

title compound

1-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester

Solvents

DMF

Conditions

Workup

1. 1
   Temperaturecooled to RT
2. 2
   workup.ADDITIONpoured
3. 3
   Extractionextracted twice with CH2Cl2
4. 4
   Washthe organic phases were washed with water
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated
8. 8
   OtherThe residue was purified by flash column chromatography (n-heptane:EtOAc 1:0-8:2)

Procedure

2.10 g (5.0 mmol) of 1-(3-bromo-phenyl)-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester and 1.82 g (10.0 mmol) of (E)-2-(4-chlorophenyl)vinyl boronic acid were dissolved in 50 ml of DMF. 12.5 ml of anhydrous potassium phosphate (tribasic, 2 M in water) were added drop by drop below 25° C., followed by 0.29 g (0.2 mmol) of tetrakis-(triphenylphosphine)-palladium. The reaction mixture was then stirred at 80° C. for 20 hours, cooled to RT, poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (n-heptane:EtOAc 1:0-8:2) to afford the title compound as light yellow solid. MS: 395.0 (MH+, 1 Cl).

Source