تفاعل #46572

معادلة التفاعل

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

المردود 58.5%

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

المردود 58.5%

المذيبات

propionitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةat reflux overnight
3. 3
   ترشيحThe dark mixture was filtered through a pad of Celite®
4. 4
   غسيلthe filter pad was rinsed with acetonitrile (250 mL)
5. 5
   تركيزThe filtrate was concentrated in vacuo
6. 6
   أخرىthe residue was purified by flash chromatography on silica gel (ethyl acetate)

الإجراء التجريبي

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)+.

المصدر