반응 #45395

반응 방정식

suspension

3-bromothieno[3,2-c]pyridin-4(5H)-one

POCl3

→

3-bromo-4-chlorothieno[3,2-c]pyridine

반응 조건

후처리

1. 1
   온도to reflux for 2.5 hours
2. 2
   추출extracted repeatedly with dichloromethane
3. 3
   세척The combined extracts were washed with water and brine
4. 4
   건조dried (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by flash column chromatography on silica gel with 0 to 5% methanol/dichloromethane

실험 절차

A suspension of Example 1A (35.91 g, 0.156 mol) in POCl3 (80 mL) was heated to reflux for 2.5 hours, cooled to room temperature, poured onto 800 g of ice, and extracted repeatedly with dichloromethane. The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 0 to 5% methanol/dichloromethane to provide 29.3 g of 3-bromo-4-chlorothieno[3,2-c]pyridine (mp 158-159° C.), which was diluted with dioxane (500 mL) and concentrated aqueous NH3 (500 mL), heated to 150° C. under pressure (260 psi) for 20 hours, and concentrated. The residue was triturated from MTBE then from methanol to provide 20.29 g of the desired product. m.p. 153-155° C.

출처