Reacción #1350576

ord-1b75261940f74050a4f94afbfe33d6b0

Ecuación de reacción

COc1cccc(CC(=O)Cl)c1
3-methoxyphenylacetyl chloride
Cn1cc(Br)c(-c2cccc(N)c2)n1
3-(3-aminophenyl)-4-bromo-1-methylpyrazole
CCN(CC)CC
triethylamine
COc1cccc(CC(=O)Nc2cccc(-c3nn(C)cc3Br)c2)c1
title compound
Rendimiento 19.0%
COc1cccc(CC(=O)Nc2cccc(-c3nn(C)cc3Br)c2)c1
N-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl]-2-(3-methoxyphenyl)acetamide
Rendimiento 19.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06541209B1uspto-grants-2003_04