반응 #495219

반응 방정식

2,6-lutidine

4-Iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde

4-fluorophenylboronic acid

myristic acid

4-fluorophenylboronic acid

→

1-(4-fluorophenyl)-4-iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde

수율 42.0%

용매

toluene

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction was stirred vigorously for an additional 3 days
2. 2
   농축The reaction mixture was concentrated in vacuo
3. 3
   workup.ADDITIONCelite® was added
4. 4
   workup.STIRRINGthe mixture was stirred for 5 minutes
5. 5
   여과Next the mixture was filtered through a plug of Celite®
6. 6
   농축concentrated in vacuo
7. 7
   여과The mixture was filtered through Celite® again
8. 8
   기타to remove additional copper that
9. 9
   기타had precipitated out
10. 10
    세척washing well with ethyl acetate
11. 11
    세척The filtrate was washed with 1N aqueous HCl
12. 12
    건조dried over sodium sulfate
13. 13
    여과filtered
14. 14
    농축concentrated under vacuum
15. 15
    기타The resulting solid was triturated with ethyl acetate

실험 절차

4-Iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde (16.0 g, 64.3 mmol), 4-fluorophenylboronic acid (26.8 g, 193 mmol, Aldrich), copper(II) acetate (23.4 g, 129 mmol, Aldrich), and myristic acid (58.7 g, 257 mmol, Aldrich) were stirred together in 800 mL of toluene. To this solution was added 2,6-lutidine (60 mL, 514 mmol, Aldrich) and the reaction was stirred vigorously for 1 day. An additional 5 g of 4-fluorophenylboronic acid was added and the reaction was stirred vigorously for an additional 3 days. The reaction mixture was concentrated in vacuo and the resulting material was suspended in 10% methanol/ethyl acetate. Celite® was added and the mixture was stirred for 5 minutes. Next the mixture was filtered through a plug of Celite®, concentrated in vacuo, and the resulting material was suspended in ethyl acetate and water. The mixture was filtered through Celite® again to remove additional copper that had precipitated out, washing well with ethyl acetate. The filtrate was washed with 1N aqueous HCl, dried over sodium sulfate, filtered, and concentrated under vacuum. The resulting solid was triturated with ethyl acetate to yield 9.25 g (42%) of 1-(4-fluorophenyl)-4-iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde as a yellow solid. The filtrate was concentrated in vacuo and the remaining solid was triturated again with ethyl acetate to yield an additional 5.75 g (68% total yield) of the desired product as a yellow solid. 1H NMR (DMSO-d6) δ 9.57 (s, 1H), 7.68 (d, 1H, J=7.2 Hz), 7.58-7.54 (m, 2H), 7.40 (t, 2H, J=8.8 Hz), 7.02 (d, 1H, J=7.2 Hz); MS (ESI+) m/z 344.13 (M+H)+.

출처