Water → 2-(2-Fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone

Temperature

-78 °C

Under an argon atmosphere, a solution of diisopropylamine (44 mL, 0.31 mol) in anhydrous tetrahydrofuran (300 mL) was cooled to −78° C., and to this was added dropwise a 1.6 M n-butyllithium hexane solution (190 mL, 0.31 mol) with stirring. After completion of the addition, the solution was stirred for 10 minutes, subsequently, a solution of 2-fluoro-4-methylpyridine (34.5 g, 0.31 mol) in anhydrous tetrahydrofuran (30 mL) was added. The reaction mixture was stirred for 30 minutes at −10° C. The reaction solution was cooled to −78° C., and a solution of N-(3-methylbenzoyl)propyleneimine (52 g, 0.30 mol) in anhydrous tetrahydrofuran (30 mL) was added dropwise. After completion of the addition, the mixture was stirred for 2 hours at room temperature. To the reaction mixture was added water (100 mL), and extracted with ethyl acetate. The extracted solution was washed with water, dried, then, the solvent was distilled off. The residue was recrystallized from isopropyl ether to obtain a title compound (35 g, yield 52%).

1. additionAfter completion of the addition
2. stirringthe solution was stirred for 10 minutes
3. stirringThe reaction mixture was stirred for 30 minutes at −10° C
4. additionAfter completion of the addition
5. stirringthe mixture was stirred for 2 hours at room temperature
6. extractionextracted with ethyl acetate
7. washThe extracted solution was washed with water
8. customdried
9. distillationthe solvent was distilled off
10. customThe residue was recrystallized from isopropyl ether

ORD record

ord-bbd2c0efbfb9483888e56ff24a6de0f5

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495018B2