Methyl Benzoate → 1-Phenyl-2-pyrazin-2-yl ethanone

To a mixture of diisopropyl-amine (1.29 g, 12.7 mmol) in anhydrous THF (10 mL) was added n-BuLi (2.5 M/L in hexane, 4.7 mL, 11.7 mmol) at −78° C., after being stirred for 30 minutes, a solution of 2-methylpyrazine (1 g, 10.6 mmol) in THF (5 mL) was added, and the mixture was stirred at −78° C. for 30 minutes, a solution of methyl benzoate (1.4 g, 10.6 mmol) in THF (5 mL) was added, and the mixture was stirred at this temperature for 3 hours. When TLC indicated that the starting material was consumed, the reaction mixture was diluted with EtOAc, and the mixture was washed with water and brine, and concentrated. The residue was purified by column chromatography (PE:EtOAc=30:1) to give Intermediate 26 (700 mg, yield 33.3%).

1. stirringthe mixture was stirred at −78° C. for 30 minutes
2. stirringthe mixture was stirred at this temperature for 3 hours
3. customwas consumed
4. additionthe reaction mixture was diluted with EtOAc
5. washthe mixture was washed with water and brine
6. concentrationconcentrated
7. customThe residue was purified by column chromatography (PE:EtOAc=30:1)

ORD-Eintrag

ord-b8f4098b51da454b93c0b1865eaa70e2

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09067893B2