Selenium Dioxide → 3-Bromopyridine-2-carbaldehyde
反応式
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[Se](=O)=[O:10]>O1CCOCC1>[Br:1][C:2]1[C:3]([CH:8]=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1参加物
4
実験手順
To a solution of 3-bromo-2-picoline (prepared as described by Guthikonda, R. N.; Cama, L. D.; Quesada, M.; Woods, M. F.; Salzmann, T. N.; Christensen, B. G. J. Med. Chem. 1987, 30, 871–880) (249 mg, 1.45 mmol) in dioxane (2 mL) was added selenium(IV) oxide (212 mg, 1.91 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ether, 3:1) to afford the title compound (78 mg, 29%) as a pale yellow solid. 1H NMR (CDCl3): δ 7.38 (dd, 1H, J=9, 6 Hz), 8.05 (d, 1H, J=9 Hz), 8.76 (d, 1H, J=3 Hz), 10.25 (s, 1H).
後処理
- temperatureat reflux overnight
- concentrationThe reaction mixture was concentrated under reduced pressure
- custompurified by column chromatography on silica gel (Hexanes/ether, 3:1)
出典と根拠
- ORDレコード
- ord-493790f571d847c0aaa1ed77fe3bc67c
- 出典データセット
- uspto-grants-2006_08
- 特許番号
- US07084155B2
反応ノート
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