Reaktion #1525224

Reaktionsgleichung

N-methyl-hydrazinecarboxylic acid tert-butyl ester

Intermediate 1

N-methyl-hydrazinecarboxylic acid tert-butyl ester

2-chloro-5-fluorophenylboronic acid

triethylamine

→

N′-(2-chloro-5-fluoro-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester

Ausbeute 27.0%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool
2. 2
   Sonstigepurified by chromatography
3. 3
   Wascheneluting with 20-40% ethyl acetate/hexanes

Vorschrift

A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 650 mg, 4.4 mmol), 2-chloro-5-fluorophenylboronic acid (Aldrich; 760 mg, 4.35 mmol), copper(II) acetate (807 mg, 4.4 mmol) and triethylamine (623 μL, 4.4 mmol) in 1,2-dichloroethane (4.5 mL) was heated in an oil bath at 50° C. for 3 h. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 40 g column, eluting with 20-40% ethyl acetate/hexanes, to give N′-(2-chloro-5-fluoro-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (322 mg, 27%) as a colorless oil.

Quelle