Reaktion #1350576

ord-1b75261940f74050a4f94afbfe33d6b0

Reaktionsgleichung

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
Ausbeute 19.0%
COc1cccc(CC(=O)Nc2cccc(-c3nn(C)cc3Br)c2)c1
N-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl]-2-(3-methoxyphenyl)acetamide
Ausbeute 19.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06541209B1uspto-grants-2003_04