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

Temperature

-78 °C

A solution of diisopropylamine (44 mL, 0.31 mol) in anhydrous tetrahydrofuran (300 mL) was cooled to −78° C. under argon atmosphere and a 1.6M solution of n-butyllithium in hexane (190 mL, 0.31 mol) was added dropwise to the solution. After complete addition, the mixture was stirred for 10 minutes and 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 at −10° C. for 30 minutes. 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 complete addition, the mixture was stirred at room temperature for 2 hours. Water (100 mL) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off. The residue was recrystallized from isopropyl ether to obtain 35 g (yield 52%) of the title compound.

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

ORD record

ord-5f3a0f9aac0f4c2a9971a1c9ad66eabf

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07276527B2