Reaktion #1379888

Reaktionsgleichung

5-Aminoquinoline

methyl 4-bromobenzoate

Cs2CO3

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

5-aminoquinoline

→

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle