反応 #1379888

反応方程式

5-Aminoquinoline

methyl 4-bromobenzoate

Cs2CO3

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

5-aminoquinoline

→

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

溶媒

toluene

反応条件

後処理

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

実験手順

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.

出典