Piperidine → 2-Fluoro-4-piperidin-1-ylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

4-bromo-2-fluorobenzonitrile (119 mg, 0.59 mmol), Piperidine (0.059 mL, 0.59 mmol), Palladium(II) acetate (6.68 mg, 0.03 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (14.18 mg, 0.03 mmol) and sodium tert-butoxide (57.2 mg, 0.59 mmol) were suspended in toluene (4 mL) and tBuOH (0.800 mL) and heated to 160°C for 10 minutes in the microwave. LCMS indicated incomplete reaction, thus, the reaction mixture was heated to 160°C for a further 20 minutes. Still incomplete reaction however, the reaction mixture was diluted with EtOAc (10 mL), and washed sequentially with water (10 mL), and saturated brine (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. A yellow oil (60mg) was isolated but NMR revealed this not be the desired product. No further work done.

Provenance & Evidence