Reacción #1379888

Ecuación de reacción

5-Aminoquinoline

methyl 4-bromobenzoate

Cs2CO3

rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

5-aminoquinoline

→

4-(quinolin-5-ylamino)-benzoic Acid Methyl Ester

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe filtrates were evaporated under reduced pressure
2. 2
   OtroThe resultant residue was purified by column chromatography on silica gel eluting with a (1:1) mixture of hexane and ethyl acetate
3. 3
   OtroThe elute was collected
4. 4
   Otrothe solvent was removed under reduced pressure
5. 5
   Otroto yield the product (
6. 6
   Otrowas used in the next stage without further purification

Procedimiento

5-Aminoquinoline (14.4 g, 0.10 mol), methyl 4-bromobenzoate (21.6 g, 0.10 mol), Cs2CO3 (45.6 g, 0.14 mol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.96 g, 1.5 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.44 g, 0.5 mmol) were mixed in toluene (15 ml) and stirred at 100° C. for 170 h. At the end of this time the reaction mixture was screened and the filtrates were evaporated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with a (1:1) mixture of hexane and ethyl acetate. The elute was collected and the solvent was removed under reduced pressure to yield the product (contaminated with a small amount of 5-aminoquinoline) which was used in the next stage without further purification.

Fuente