[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:15]I.[OH-].[K+]>CN(C=O)C.O>[CH3:15][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1
Indole-5-carboxylic acid (200 mg, 1.24 mmol) was dissolved in DMF (2 mL), and the solution was added with 60% sodium hydride-mineral oil dispersant (164 mg, 4.1 mmol), followed by stirring at room temperature for 10 minutes. The mixture was added with methyl iodide (0.258 mL, 0.410 mmol), stirred at room temperature for 3 hours and then added with 4 mol/L aqueous potassium hydroxide solution (2 mL), followed by stirring at 80° C. for 5 hours. The reaction mixture was added with water, and the organic layer was separated from aqueous layer. The aqueous layer was added with 1 mol/L hydrochloric acid to adjust the pH to 1, followed by stirring at room temperature for 1 hour. The obtained solid was collected by filtration and dried under reduced pressure to obtain 1-methylindole-5-carboxylic acid (142 mg, yield 65%).
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