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0 °C

1.0 g (5.8 mmol) of 4-bromo-2-methylpyridine and 2.14 g (11.6 mmol) of ethyl 4-chlorobenzoate are placed under a stream of argon in a round-bottomed flask and dissolved in 10 ml of anhydrous tetrahydrofuran. The solution is cooled to 0° C. and 12 ml of a lithium hexamethyldisilazane (LiHMDS) solution (1M in tetrahydrofuran) are added. After addition, the mixture is heated at 45° C. for 3 h and cooled to ambient temperature, and then water is added. The tetrahydrofuran is subsequently evaporated under reduced pressure and the aqueous phase is extracted three times with ether. The organic phase is separated, dried and concentrated under reduced pressure. The residue obtained is purified by chromatography on silica gel, elution being carried out with a mixture of dichloromethane and heptane. 1.11 g (62%) of compound are obtained.

1. additionAfter addition
2. temperaturethe mixture is heated at 45° C. for 3 h
3. temperaturecooled to ambient temperature
4. customThe tetrahydrofuran is subsequently evaporated under reduced pressure
5. extractionthe aqueous phase is extracted three times with ether
6. customThe organic phase is separated
7. customdried
8. concentrationconcentrated under reduced pressure
9. customThe residue obtained
10. customis purified by chromatography on silica gel, elution
11. additionbeing carried out with a mixture of dichloromethane and heptane