반응 #43412

반응 방정식

Potassium carbonate

water

pyridine tris(1-methylethenyl)boroxin

water

8-bromo-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine

→

3,7-Difluoro-8-(1-methylethenyl)-2-(methyloxy)-1,5-naphthyridine

용매

ether

dimethoxyethane

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux for 5 hours
3. 3
   기타The phases were separated
4. 4
   추출the aqueous phase further extracted with ether (2×200 ml)
5. 5
   건조The combined organic extracts were dried over magnesium sulphate
6. 6
   기타evaporated
7. 7
   기타The residue was chromatographed on silica eluting with a gradient of 0-50% ethyl acetate in hexane affording a white solid (820 mg, 84%)

실험 절차

A solution of 8-bromo-3,7-difluoro-2-(methyloxy)-1,5-naphthyridine (1.14 g, 4.15 mmol) and tetrakis(triphenylphosphine)palladium(0) (240 mg, 0.21 mmol) in degassed dimethoxyethane (40 ml) was stirred under argon for 30 minutes. Potassium carbonate (570 mg, 4.2 mmol), water (12 ml) and pyridine-tris(1-methylethenyl)boroxin (1:1) (470 mg, 1.66 mmol) were added the mixture was heated to reflux for 5 hours. The cooled mixture was treated with water (100 ml) and ether (200 ml). The phases were separated and the aqueous phase further extracted with ether (2×200 ml). The combined organic extracts were dried over magnesium sulphate and evaporated. The residue was chromatographed on silica eluting with a gradient of 0-50% ethyl acetate in hexane affording a white solid (820 mg, 84%).

출처