Sodium Azide → 4-Azido-5-fluoropyridine-3-carbaldehyde
反応式
Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C>[N:11]([C:2]1[C:7]([F:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH:9]=[O:10])=[N+:12]=[N-:13]参加物
4
実験手順
A mixture of 4-chloro-5-fluoro-pyridine-3-carbaldehyde (4.15 g, 26.0 mmol) and sodium azide (1.86 g, 28.6 mmol) in DMF (15 mL) was stirred at room temperature for 18 hours. The reaction mixture was quenched with brine (200 mL) and extracted with ethyl acetate (3×75 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane) to afford the title compound as an off-white solid (3.61 g, 84% yield). 1H NMR (300 MHz, CDCl3): δ 10.32 (s, 1H), 8.79 (s, 1H), 8.58 (d, J=3.0 Hz, 1H).
後処理
- customThe reaction mixture was quenched with brine (200 mL)
- extractionextracted with ethyl acetate (3×75 mL)
- dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane)
出典と根拠
- ORDレコード
- ord-e55fdf518d124993aabeb96dfa3d26cc
- 出典データセット
- uspto-grants-2016_04
- 特許番号
- US09309240B2
反応ノート
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