反应详情

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) were combined in toluene (700 mL), treated 2,6-lutidine (45 mL, 385 mmol), and stirred vigorously 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 and then suspended in 10% methanol/EtOAc. Diatomaceous earth was added and the mixture was stirred for 5 minutes. The mixture was filtered through a plug of diatomaceous earth. The filtrate was concentrated, and suspended in EtOAc and water. The mixture was again filtered through diatomaceous earth, rinsing forward with EtOAc. The filtrate was washed with 1N HCl, dried over Na2SO4, and concentrated under vacuum. The resulting solid was triturated with EtOAc to yield 1-(4-fluorophenyl)-4-iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde (8.0 g, 42% yield) as a yellow solid.

1. stirringthe reaction was stirred vigorously for an additional 3 days
2. concentrationThe reaction mixture was concentrated
3. additionDiatomaceous earth was added
4. stirringthe mixture was stirred for 5 minutes
5. filtrationThe mixture was filtered through a plug of diatomaceous earth
6. concentrationThe filtrate was concentrated
7. filtrationThe mixture was again filtered through diatomaceous earth
8. washrinsing forward with EtOAc
9. washThe filtrate was washed with 1N HCl
10. dry with materialdried over Na2SO4
11. concentrationconcentrated under vacuum
12. customThe resulting solid was triturated with EtOAc