Method for methylation reaction
A methylation and reaction technology, applied in the field of methylation reaction, can solve the problems of narrow substrate application range, high toxicity of methylation reagents, low reactivity, etc. simple effect
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Embodiment 1
[0020] Preparation of 1-methyl-4-nitroindole
[0021]
[0022] Add 4-nitroindole (100 mg, 0.62 mmol), DMF (4 mL), NaH (60% dispersed in mineral oil, 74 mg, 1.85 mmol, 3eq.) into the reaction flask in turn, and stir at room temperature for 5 minutes Finally, after the NaH was uniformly dispersed, slowly inject methyl trifluoroacetate (0.25 mL, 2.48 mmol, 4 eq.) into the reaction bottle, and after 4 hours of reaction, TLC plate, the raw material point disappeared, that is, the reaction was complete, stop Stir. Extracted twice with ethyl acetate and distilled water, washed with saturated NaCl solution, combined organic phase, dried organic phase with anhydrous magnesium sulfate, filtered to remove magnesium sulfate, rotary evaporated to remove solvent, and purified by column chromatography to obtain yellow solid 1-formazan yl-4-nitroindole (106 mg, 98% yield). 1 H NMR (400 MHz, CDCl 3 ) δ8.17 (dd, J = 8.0,0.6 Hz, 1H), 7.67 (d, J = 8.1 Hz, 1H), 7.32 (dd, J = 13.9, 5.7 ...
Embodiment 2
[0024] Preparation of 1-methyl-5-nitroindole
[0025]
[0026] Add 5-nitroindole (100 mg, 0.62 mmol), DMF (4 mL), NaH (60% dispersed in mineral oil, 74 mg, 1.85 mmol, 3eq.) into the reaction flask in turn, and stir at room temperature for 5 minutes Finally, after the NaH was evenly dispersed, slowly inject methyl trifluoroacetate (0.25 mL, 2.48 mmol, 4 eq.) into the reaction flask, and after 4 hours of reaction, TLC spotting, the raw material point disappeared, that is, the reaction was complete, stop Stir. Extracted twice with ethyl acetate and distilled water, washed with saturated NaCl solution, combined organic phase, dried organic phase with anhydrous magnesium sulfate, filtered to remove magnesium sulfate, rotary evaporated to remove solvent, and purified by column chromatography to obtain yellow solid 1-formazan yl-5-nitroindole (101 mg, 93% yield). 1 H NMR (400 MHz, CDCl 3 ) δ8.57 (d, J = 1.9 Hz,1H), 8.11 (dd, J = 9.1, 2.1 Hz, 1H), 7.33 (d, J = 9.1 Hz, 1H),...
Embodiment 3
[0028] Preparation of 1-methyl-4-bromoindole
[0029]
[0030] Add 4-bromoindole (100 mg, 0.51 mmol), DMF (4 mL), potassium tert-butoxide (17 2mg, 1.53 mmol, 3eq.) into the reaction flask in turn, stir at room temperature for 5 minutes, and wait for tert-butanol to After the potassium was uniformly dispersed, methyl trifluoroacetate (0.20 mL, 2.0 mmol, 4 eq.) was slowly injected into the reaction flask. After 4 hours of reaction, TLC spotting showed that the raw material point disappeared, that is, the reaction was complete, and the stirring was stopped. Extracted twice with ethyl acetate and distilled water, washed with saturated NaCl solution, combined organic phase, dried organic phase with anhydrous magnesium sulfate, filtered to remove magnesium sulfate, rotary evaporated to remove solvent, and purified by column chromatography to obtain light green liquid 1 -Methyl-4-bromoindole (100 mg, 93% yield). 1 H NMR (400 MHz, CDCl 3 ) δ 7.35 (dd, J = 7.6, 0.6 Hz,1H), 7.30 (d...
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