Reaction #46572

Reaction equation

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

Yield 58.5%

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

Yield 58.5%

Solvents

propionitrile

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureat reflux overnight
3. 3
   FiltrationThe dark mixture was filtered through a pad of Celite®
4. 4
   Washthe filter pad was rinsed with acetonitrile (250 mL)
5. 5
   ConcentrationThe filtrate was concentrated in vacuo
6. 6
   Otherthe residue was purified by flash chromatography on silica gel (ethyl acetate)

Procedure

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)+.

Source