反応 #2286394

反応方程式

di(tert-butyl) 2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate

F-TEDA

Water

→

solid

収率 82.2%

di(tert-butyl) 4-fluoro-2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate

収率 82.2%

溶媒

acetonitrile

DMF

反応条件

後処理

1. 1
   抽出the target extracted with ethyl acetate (2×)
2. 2
   乾燥The organic layer was dried over sodium sulfate
3. 3
   ろ過was filtered
4. 4
   濃縮was concentrated
5. 5
   その他The crude mixture was purified via silica gel chromatography (0-100% ethyl acetate/hexanes)

実験手順

To a degassed solution of di(tert-butyl) 2-(5-fluoropyridin-3-yl)-1,3-thiazol-5-ylimidodicarbonate (1.0 g, 2.53 mmol) in anhydrous acetonitrile (20 mL) and DMF (10 mL) was added F-TEDA (SELECTFLUOR™) (1.8 g, 5.06 mmol). The reaction mixture was stirred at ambient temperature for 7 days. Water was added to the reaction mixture and the target extracted with ethyl acetate (2×). The organic layer was dried over sodium sulfate, was filtered and was concentrated. The crude mixture was purified via silica gel chromatography (0-100% ethyl acetate/hexanes) to afford a beige solid (860 mg, 82%): mp 143-143° C.; 1H NMR (300 MHz, CDCl3) δ 8.87 (t, J=1.4 Hz, 1H), 8.54 (d, J=2.7 Hz, 1H), 7.91 (ddd, J=8.9, 2.7, 1.8 Hz, 1H), 1.48 (s, 18H); ESIMS m/z 414 (M+1).

出典