반응 #46572

반응 방정식

3-bromo-5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-one

tert-butyl acrylate

DIEA

P(o-tol)3

N2

→

title compound

수율 58.5%

tert-butyl (E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylate

수율 58.5%

용매

propionitrile

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도at reflux overnight
3. 3
   여과The dark mixture was filtered through a pad of Celite®
4. 4
   세척the filter pad was rinsed with acetonitrile (250 mL)
5. 5
   농축The filtrate was concentrated in vacuo
6. 6
   기타the residue was purified by flash chromatography on silica gel (ethyl acetate)

실험 절차

A solution of 3-bromo-5,6,7,9-tetrahydro-pyrido[2,3-b]azepin-8-one (1.00 g, 4.15 mmole), tert-butyl acrylate (0.67 mL, 4.60 mmole), DIEA (1.45 mL, 8.30 mmole), Pd(OAc)2 (0.09 g, 0.42 mmole) and P(o-tol)3 (0.25 g, 0.85 mmole) in propionitrile (25 mL) was purged with N2 and then heated at reflux overnight. The dark mixture was filtered through a pad of Celite®, and the filter pad was rinsed with acetonitrile (250 mL). The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (ethyl acetate). The title compound (0.70 g, 58%) was obtained as a light yellow solid after drying in vacuo: MS (ES) m/e 289 (M+H)+.

출처