반응 #77846

반응 방정식

tert-butyl 3-(5-bromopyridin-2-yl)prop-2-ynylcarbamate

N-Cbz propargylamine

→

6-1

수율 55.1%

Benzyl 3-(6-{3-[(tert-butoxycarbonyl)amino]prop-1-ynyl}pyridin-3-yl)prop-2-ynylcarbamate

수율 55.1%

용매

diisopropylamine

ethyl acetate

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux under a nitrogen atmosphere for 3 hours
3. 3
   여과The precipitates were filtered
4. 4
   세척rinsed with ethyl acetate (30 mL)
5. 5
   농축concentrated under reduced pressure
6. 6
   기타purified by silica gel column chromatography
7. 7
   workup.ADDITIONa mixture of MTBE and hexanes (2:3 to 4:1)
8. 8
   workup.ADDITIONThe fractions containing the product
9. 9
   농축concentrated under reduced pressure
10. 10
    기타The residue was crystallized from MTBE
11. 11
    여과Crystals were filtered
12. 12
    세척washed with MTBE
13. 13
    기타dried

실험 절차

A mixture of tert-butyl 3-(5-bromopyridin-2-yl)prop-2-ynylcarbamate (3-1) (1.44 g), N-Cbz propargylamine (1.09 g), Pd(PPh3)2Cl2 (73 mg), and CuI (10 mg) in diisopropylamine (25 mL) was heated under reflux under a nitrogen atmosphere for 3 hours. The mixture was cooled to ambient temperature and diluted with ethyl acetate (70 mL). The precipitates were filtered and rinsed with ethyl acetate (30 mL). The filtrate and washings were combined, concentrated under reduced pressure, and purified by silica gel column chromatography using a mixture of MTBE and hexanes (2:3 to 4:1). The fractions containing the product were combined and concentrated under reduced pressure. The residue was crystallized from MTBE. Crystals were filtered, washed with MTBE, and dried to give 6-1 (1.07 g). An additional 120 mg of 6-1 was isolated from the mother liquors and washings.

출처