반응 #436365

반응 방정식

potassium carbonate

{3-bromo-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazin-2-yl}[(4-methoxyphenyl)methyl]amine

ethylboronic acid

→

{3-ethyl-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazin-2-yl}[(4-methoxyphenyl)methyl]amine

수율 92.8%

용매

sodium hydroxide

toluene

반응 조건

후처리

1. 1
   온도The mixture is heated to 85 C for 8 hours
2. 2
   추출extracted twice with 1:1 hexane-ethyl ether
3. 3
   건조The combined extracts are dried (sodium sulfate)
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타The residue is purified by flash chromatography
7. 7
   세척eluting with 20% ether in hexanes

실험 절차

Tetrakis(triphenylphosphine)palladium(0) (50 mg) and potassium carbonate (2.0 M, 1.0 mL) are added to a stirred solution of {3-bromo-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazin-2-yl}[(4-methoxyphenyl)methyl]amine (514 mg, 1.0 mmol) and ethylboronic acid (219 mg, 3.0 mmol) in toluene (8 mL). The mixture is heated to 85 C for 8 hours, cooled to room temperature, diluted with 2.0 M sodium hydroxide and extracted twice with 1:1 hexane-ethyl ether. The combined extracts are dried (sodium sulfate), filtered and concentrated. The residue is purified by flash chromatography, eluting with 20% ether in hexanes to give {3-ethyl-6-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazin-2-yl}[(4-methoxyphenyl)methyl]amine (430 mg).

출처