Reaction #46486

Reaction equation

2-amino-5-bromopyridine

benzyl acrylate

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

Yield 39.3%

Benzyl (E)-3-(6-aminopyridin-3-yl)acrylate

Yield 39.3%

Solvents

propionitrile

Conditions

Workup

1. 1
   Temperatureat reflux overnight
2. 2
   FiltrationThe dark mixture was filtered through Celite®
3. 3
   Concentrationthe filtrate was concentrated

Procedure

A solution of 2-amino-5-bromopyridine (2.25 g, 13.0 mmole), benzyl acrylate (3.2 g, 19.7 mmole), Pd(OAc)2 (0.31 g, 1.4 mmole), tri-ortho-tolylphosphine (0.73 g, 2.4 mmole), and diisopropylethylamine (3.5 mL, 20.0 mmole) in propionitrile (50 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica gel (3% MeOH/CH2Cl2) gave the title compound (1.3 g, 39%): MS (ES) m/e 255 (M+H)+.

Source