Reacción #7572

Ecuación de reacción

tri(n-butyl)phosphine

4-chloro-7-hydroxy-6-methoxycinnoline

4-hydroxymethylpyridine

hydrogen chloride

isopropanol

1,1′-(azodicarbonyl)dipiperidine

→

4-chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride

Rendimiento 122.0%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe resulting solid was filtered off
2. 2
   Lavadowashed with methylene chloride and ether

Procedimiento

The starting material, 4-chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride, was obtained by adding 4-chloro-7-hydroxy-6-methoxycinnoline (200 mg, 0.95 mmol), followed by 4-hydroxymethylpyridine (108 mg, 1 mmol) and 1,1′-(azodicarbonyl)dipiperidine (647 mg, 2.5 mmol), in portions, to a solution of tri(n-butyl)phosphine (640 μg, 2.5 mmol) in methylene chloride (6 ml). After stirring for 1 hour at ambient temperature, a solution of 7M hydrogen chloride in isopropanol (300 μl, 2.1 mmol) was added. The resulting solid was filtered off, washed with methylene chloride and ether to give 4-chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride as a solid (196 mg, 55%).

Fuente