Example 1 Synthesis of JWH4511-ethyl-2-methylindole: To a reaction vial containing 0.20 g (1.52 mmol) of 2-methylindole was added 6 mL of a DMSO-dissolved solution of 0.38 g (6.89 mmol) of KOH, followed by 0.24 mL (3.04 mmol) of ethyl iodide. The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the reaction was quenched by the addition of 15 mL of water and extracted with ethyl acetate (2 x 15 mL). The organic phases were combined, washed sequentially with water (10 mL) and brine (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (eluent: ethyl ether/petroleum ether=0.5:9.5) to afford 0.20 g (83% yield) of the target compound N-ethyl-2-methylindole as a red oil.
[1] Patent: WO2012/24670, 2012, A2. Location in patent: Page/Page column 43
[2] Synthesis, 1981, # 5, p. 389 - 390
[3] Organic Letters, 2017, vol. 19, # 17, p. 4680 - 4683
