Réaction #1379888

Équation de réaction

5-Aminoquinoline

methyl 4-bromobenzoate

Cs2CO3

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

5-aminoquinoline

→

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

Solvants

toluene

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source