Reaction #1379888

Reaction equation

5-Aminoquinoline

methyl 4-bromobenzoate

Cs2CO3

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

5-aminoquinoline

→

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

Solvents

toluene

Conditions

Workup

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

Procedure

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