반응 #306408

반응 방정식

cesium carbonate

1-(6-chloro-3-fluoropyridin-2-yl)-2,2-difluoro-2-(quinolin-6-yl)ethanone oxime

3,5-difluorophenylboronic acid

DMF

→

product

수율 9.0%

6-((5-(3,5-difluorophenyl)isoxazolo[5,4-b]pyridin-3-yl)difluoromethyl)quinoline

수율 9.0%

용매

water

반응 조건

후처리

1. 1
   기타The mixture flushed with argon
2. 2
   기타sealed
3. 3
   농축The suspension was concentrated
4. 4
   기타triturated with water
5. 5
   여과filtered
6. 6
   기타to afford
7. 7
   기타a tan solid, purification by MPLC (
8. 8
   세척eluted with a gradient of 20 to 50% ethyl acetate in hexanes)

실험 절차

To a pressure vessel was added cesium carbonate (0.61 g, 1.9 mmol), PdCl2(dppf)-CH2Cl2 adduct (26 mg, 0.031 mmol), 1-(6-chloro-3-fluoropyridin-2-yl)-2,2-difluoro-2-(quinolin-6-yl)ethanone oxime (0.26 g, 0.63 mmol) and 3,5-difluorophenylboronic acid (0.15 g, 0.94 mmol) in anhydrous DMF (5 mL) and water (1 mL). The mixture flushed with argon, sealed and stirred at 80° C. for one hour. The suspension was concentrated, triturated with water and filtered to afford a tan solid, purification by MPLC (eluted with a gradient of 20 to 50% ethyl acetate in hexanes) afforded the product as a white solid (23 mg, 9%). MS m/z=410.0 [M+1]+ Calc'd for C22H11F4N3O: 409.3.

출처