反应详情

2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (5.99 g, 15.79 mmol) was added portionwise to 2-fluoro-5-iodobenzoic acid (3.000 g, 11.28 mmol), 4-methoxypiperidine (1.364 g, 11.84 mmol) and triethylamine (3.93 mL, 28.19 mmol) in DMF (40 mL). The resulting solution was stirred at room temperature for 7 hours. The reaction mixture was poured into water (350 mL), extracted with Et2O (2×200 mL), the combined organic layers were washed with saturated brine (100 mL), dried over Na2SO4, filtered and evaporated to afford a dark orange gum. The crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford the desired material as a colourless gum (0.348 g, 67% yield); 1H NMR (400.132 MHz, CDCl3) δ1.57-1.99 (4H, m), 3.18 (1H, m), 3.39 (3H, s), 3.50 (2H, m), 3.63 (1H, m), 3.98 (1H, m), 6.89 (1H, t), 7.69 (2H, m); m/z (LC-MS, ESI+), RT=2.05 (M+H 364.0).

1. extractionextracted with Et2O (2×200 mL)
2. washthe combined organic layers were washed with saturated brine (100 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. customevaporated
6. customto afford a dark orange gum
7. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in isohexane
8. customPure fractions were evaporated to dryness