反应详情

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0 °C

To a 25 mL round bottom flask was weighed 7 (51 mg, 0.2 mmol) and was added DMF (2 mL) to afford a solution. The flask was purged with argon for five min followed by cooling down to 0° C. using ice bath. Sodium hydride (14.4 mg, 0.6 mmol) was added to the solution at 0° C. The solution was stirred for 30 min at 0° C. under argon atmosphere. Dimethyl sulfate (75.7 mg; ≈57 μl; 0.6 mmol) was injected to the reaction mixture and the flask was warmed to room temperature. The mixture was stirred at room temperature for another 3 h at the end of which 1 N Hydrochloric acid (5 mL) was added carefully to quench the reaction followed by water (20 mL) to afford a precipitate. Product was extracted using ethyl acetate (10 mL×2). Combined organic extracts were washed with brine (10 mL) dried (anhydrous sodium sulfate) and concentrated under reduced pressure. Silica gel (200 mg) was added and solvent evaporated to afford a plug. Column chromatography by elution with hexanes:ethyl acetate (5:1) afforded AAG16 (20 mg; 37%) as light brown semisolid; which was triturated withl hexanes to afford light brown solid. TLC Rf0.79 (CHCl3:MeOH, 10:1); mp 84-85.6° C.; 1HNMR (400 MHz) (DMSO-d6): δ 1.036-1.039 (d, 3H, CH3, J=1.2 Hz); 3.423 (s, 3H, NCH3), 3.752 (s, 3H, OCH3), 6.944-6.967 (d, 2H, C6H4, J=9.2 Hz), 7.176-7.199 (d, 2H, C6H4, J=9.2 Hz), 7.505-7.508 (d, 1H, C6-CH, J=1.2 Hz), 8.234 (s, 1H, C2-CH). Anal. Calcd for C15H15N3O2.0.28 C6H14.0.05 HCl: C, 67.84; H, 6.48; N, 14.22; Found: C, 67.89; H, 6.18; N, 14.06.

1. customTo a 25 mL round bottom flask was weighed
2. customto afford a solution
3. customThe flask was purged with argon for five min
4. temperaturethe flask was warmed to room temperature
5. additionwas added carefully
6. customto quench the reaction
7. customto afford a precipitate
8. extractionProduct was extracted
9. washCombined organic extracts were washed with brine (10 mL)
10. dry with materialdried (anhydrous sodium sulfate)
11. concentrationconcentrated under reduced pressure
12. additionSilica gel (200 mg) was added
13. customsolvent evaporated
14. customto afford a plug
15. washColumn chromatography by elution with hexanes:ethyl acetate (5:1)
16. customafforded AAG16 (20 mg; 37%) as light brown semisolid
17. customwhich was triturated withl hexanes
18. customto afford light brown solid