Réaction #1350575

Équation de réaction

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

Rendement 26.0%

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

Rendement 26.0%

Solvants

chloroform

brine

Conditions de réaction

Traitement

1. 1
   Lavagethe organic layer washed with further brine
2. 2
   Séchagedried over magnesium sulphate
3. 3
   Concentrationconcentrated in vacuo
4. 4
   AutreThe crude product was purified by column chromatography (ethyl acetate-toluene, 1:1)

Mode opératoire

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