Reaction #1350575

Reaction equation

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

3-fluorophenylacetic acid

1-hydroxybenzotriazole hydrate

2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluoro-phosphate

N, N-Diisopropylethylamine

→

title compound

Yield 26.0%

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

Yield 26.0%

Solvents

chloroform

brine

Conditions

Workup

1. 1
   Washthe organic layer washed with further brine
2. 2
   Dryingdried 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 mixture of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (30 mg, 0.12 mmol), 3-fluorophenylacetic acid (18 mg, 0.12 mmol), 1-hydroxybenzotriazole hydrate (16 mg, 0.12 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluoro-phosphate (46 mg, 0.12 mmol) were dissolved in chloroform (1.5 ml). N, N-Diisopropylethylamine (0.02 ml, 0.13 mmol) was added and the mixture stirred at room temperature for 16 h. The reaction mixture was then poured into brine and the organic layer washed with further brine, dried over magnesium sulphate and then concentrated in vacuo. The crude product was purified by column chromatography (ethyl acetate-toluene, 1:1), giving the title compound (12 mg, 26%). Rf 0.41 (ethyl acetate-toluene, 1:1).

Source