반응 #70348

반응 방정식

5-bromo-2-(3-methoxyphenyl)pyridine

Intermediate 27

5-bromo-2-(3-methoxyphenyl)pyridine

ethyl 2-aminobenzoate

Intermediate 33

ethyl 2-aminobenzoate

BINAP

NaOtBu

→

hexane ethyl acetate

수율 98.4%

expected compound

2-(6-(3-Methoxyphenyl)pyridin-3-ylamino)benzoic acid

용매

toluene

반응 조건

후처리

1. 1
   기타The solvent was evaporated
2. 2
   기타the solid residue was triturated with aqueous solution of 2N HCl
3. 3
   추출extracted with CHCl3

실험 절차

In a schlenck tube, a mixture of 5-bromo-2-(3-methoxyphenyl)pyridine (Intermediate 27, 0.91 mmol, 0.23 g), ethyl 2-aminobenzoate (Intermediate 33, 0.91 mmol, 0.15 g), BINAP (0.05 mmol, 0.028 g), Pd2(dba)3 (0.05 mmol, 0.042 g) and NaOtBu (1.82 mmol, 0.175 g) in toluene (4 ml) was heated at 110° C. for 12 hours, under argon atmosphere. The solvent was evaporated and the solid residue was triturated with aqueous solution of 2N HCl and extracted with CHCl3. The crude mixture was purified by flash chromatography over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.078 g (yield 26%) of the expected compound.

출처