反应详情

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.

1. temperaturewas heated
2. temperatureunder reflux under a nitrogen atmosphere for 3 hours
3. filtrationThe precipitates were filtered
4. washrinsed with ethyl acetate (30 mL)
5. concentrationconcentrated under reduced pressure
6. custompurified by silica gel column chromatography
7. additiona mixture of MTBE and hexanes (2:3 to 4:1)
8. additionThe fractions containing the product
9. concentrationconcentrated under reduced pressure
10. customThe residue was crystallized from MTBE
11. filtrationCrystals were filtered
12. washwashed with MTBE
13. customdried