반응 #57785

반응 방정식

HCl

BCl3

1,2-difluoro-4aminobenzene

NaOH

4-Cyanopyridine

→

title compound

(2-Amino-4,5-difluoro-phenyl)-pyridin4-yl-methanone

용매

water

DCM

trichloroethylene

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 30 min
2. 2
   온도The solution was then heated at 80-90° C. for 1 h
3. 3
   온도The resulting solution was refluxed at 160° C. for 4 hr
4. 4
   workup.STIRRINGstirred at RT over night
5. 5
   온도refluxed at 110° C. for 1.5 h
6. 6
   온도The reaction mixture was cooled to RT
7. 7
   기타The resulting two layers were separated
8. 8
   추출the aqueous layer was extracted with DCM
9. 9
   건조dried over sodium sulphate
10. 10
    농축concentrated
11. 11
    기타The compound was purified by column chromatography

실험 절차

BCl3 (6.2 ml, 1M in DCM) was added drop wise to 1,2-difluoro-4aminobenzene (0.5 g, 0.004 mol) in trichloroethylene (6.5 ml) at 0° C. and this mixture stirred for 15 min. 4-Cyanopyridine (0.48 g, 0.005 mol) was added and the solution was warmed to RT and stirred for 30 min. The solution was then heated at 80-90° C. for 1 h. The resulting solution was refluxed at 160° C. for 4 hr and stirred at RT over night. 3N HCl was added to the reaction mixture and refluxed at 110° C. for 1.5 h. The reaction mixture was cooled to RT and made basic (pH=12) with 6N NaOH. The reaction mixture was diluted with water and DCM. The resulting two layers were separated and the aqueous layer was extracted with DCM, dried over sodium sulphate and concentrated. The compound was purified by column chromatography using silica gel to yield title compound.

출처