Réaction #44228

Équation de réaction

2-bromo-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester

trimethylsilylacetylene

iPr2NH

→

desired product

4-chloro-1,5-dimethyl-6-oxo-2-trimethylsilanylethynyl-1,6-dihydropyridine-3-carboxylic acid ethyl ester

Solvants

THF

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 16 hours
2. 2
   LavageThe organic layer is washed with saturated NH4Cl solution and brine
3. 3
   Séchagedried (MgSO4)
4. 4
   Concentrationconcentrated under reduced pressure

Mode opératoire

To a mixture of 2-bromo-4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (1.00 equivalent), trimethylsilylacetylene (1.20 equivalents) and iPr2NH (2.00 equivalents) in THF is added CuI (0.10 equivalents) followed by Pd(PPh3)2Cl2 (0.10 equivalents). After stirring the reaction mixture at reflux for 16 hours, it is cooled to room temperature and diluted with ethyl acetate. The organic layer is washed with saturated NH4Cl solution and brine, dried (MgSO4) and concentrated under reduced pressure. The desired product is obtained by flash column chromatography as necessary.

Source