2,6-Lutidine → 1-(4-Fluorophenyl)-4-iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde

Participants

Reaction Steps

A mixture of 4-iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde (12.0 g, 48.3 mmol), 4-fluorophenylboronic acid (20.1 g, 144.7 mmol), copper(II) acetate (17.55 g, 96.75 mmol), and myristic acid (44 g, 193 mmol) in toluene (700 mL) was treated with 2,6-lutidine (45 mL, 385.5 mmol) and stirred vigorously at RT for 1 day. Additional 4-fluorophenylboronic acid (5 g) was added and the reaction was stirred vigorously for an additional 3 days. The reaction mixture was concentrated to dryness, suspended in 10% MeOH/EtOAc and the solids removed via filtration through diatomaceous earth. The filtrate was concentrated to dryness, the residue treated with EtOAc and water and again filtered through diatomaceous earth. The filtrate was washed with 1N HCl, dried over Na2SO4 and concentrated to dryness. The material was treated with EtOAc and the resulting solid was collected via filtration to afford 1-(4-fluorophenyl)-4-iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde (8.0 g, 42%) as a yellow solid.

Provenance & Evidence