Diisopropylamine → 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, with stirring, a solution of 1.6M n-butyl lithium in hexane (190 mL, 0.31 mol) was added dropwise. After the completion of the dropwise addition, the mixture was stirred for 10 min. and 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 min. 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 the completion of the dropwise addition, the mixture was stirred at room temperature for 2 hrs. 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 evaporated. The residue was recrystallized from isopropyl ether to give the title compound (35 g, yield 52%).

1. additionAfter the completion of the dropwise addition
2. stirringthe mixture was stirred for 10 min.
3. stirringThe reaction mixture was stirred at −10° C. for 30 min
4. additionAfter the completion of the dropwise addition
5. stirringthe mixture was stirred at room temperature for 2 hrs
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with water
8. customdried
9. customthe solvent was evaporated
10. customThe residue was recrystallized from isopropyl ether

ORD record

ord-59bb158be304439fa970a95c4723a9a2

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199124B2