Reacción #8461

Ecuación de reacción

product

alpha-bromo-2′-fluoro-4′-chloropropoxyacetophenone

2-amino-4-picoline

→

2-(4′-chloropropoxy-2′fluorophenyl)-7-methylimidazo[1,2-a]pyridine

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvent evaporated in vacuo
2. 2
   OtroA portion of the residue was purified via silica gel chromatography (ethyl acetate/hexane) directly
3. 3
   workup.DISSOLUTIONThe remainder of the residue was dissolved in methanol/dichloromethane
4. 4
   workup.ADDITIONtreated with Dowex® 550A basic resin (Aldrich, Milwaukee, Wis.) for 10 minutes
5. 5
   OtroThe resin was removed via filtration
6. 6
   Otrothe filtrate evaporated
7. 7
   workup.ADDITIONThe combined material (0.42 g) containing the title compound
8. 8
   Otrowas used without further purification

Procedimiento

A solution of the product of Step B (1.0 g) and 2-amino-4-picoline (0.357 g) in ethanol (4 mL) was heated at 73° C. for 18 hours. The reaction mixture was cooled to ambient temperature and the solvent evaporated in vacuo. A portion of the residue was purified via silica gel chromatography (ethyl acetate/hexane) directly. The remainder of the residue was dissolved in methanol/dichloromethane and treated with Dowex® 550A basic resin (Aldrich, Milwaukee, Wis.) for 10 minutes. The resin was removed via filtration and the filtrate evaporated prior to silica gel chromatography (ethyl acetate/hexane). The combined material (0.42 g) containing the title compound was used without further purification.

Fuente