Reaction #1350576

Reaction equation

3-methoxyphenylacetyl chloride

3-(3-aminophenyl)-4-bromo-1-methylpyrazole

triethylamine

→

title compound

Yield 19.0%

N-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl]-2-(3-methoxyphenyl)acetamide

Yield 19.0%

Solvents

dichloromethane

dichloromethane

brine

Conditions

Workup

1. 1
   WashThe organic layer was washed with more brine
2. 2
   Dryingthen dried over magnesium sulphate
3. 3
   Concentrationconcentrated in vacuo
4. 4
   OtherThe crude product was purified by column chromatography (ethyl acetate-toluene, 1:1)

Procedure

A solution of 3-methoxyphenylacetyl chloride (0.02 ml, 0.12 mmol) in dichloromethane (0.75 ml) was added dropwise at 0° C. to a solution of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (30 mg, 0.12 mmol) and triethylamine (0.02 ml, 0.13 mmol) in dichloromethane (0.75 ml). The resulting mixture was stirred at room temperature for 16 h and then poured into brine. The organic layer was washed with more brine then dried over magnesium sulphate and concentrated in vacuo. The crude product was purified by column chromatography (ethyl acetate-toluene, 1:1), giving the title compound (9 mg, 19%). Rf 0.30 (ethyl acetate-toluene, 1:1).

Source