Hydrochloric Acid → HCID 58221535, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of KOtBu (1.0 g, 8.9 mmol) in benzene (20 mL) was added ethyl 5-bromo-1H-indole-2-carboxylate (2.3 g, 8.6 mmol) as a solution in benzene (40 mL) at room temperature. To the resulting white slurry was added methyl acrylate (1.5 mL, 17.1 mmol). The combined solution was heated at 80° C. for 1 h then cooled to room temperature and stirred for an additional 16 h. The reaction mixture was then poured into H2O (100 mL) and the pH was adjusted to 4 with concentrated HCl. The aqueous phase was then extracted with CH2Cl2 (2×200 mL). The combined organic phases were washed with H2O, dried over Na2SO4, filtered and concentrated. The crude residue was then dissolved in EtOH (30 mL), 4M HCl (10 mL) was added, and the mixture was heated to reflux. After stirring at reflux for 3.5 h, the reaction mixture was cooled to room temperature and neutralized with saturated aqueous NaHCO3. The aqueous phase was then washed with Et2O (2×100 mL). The combined organic phase was dried over MgSO4, filtered, and concentrated to afford the title compound as an off white solid (1.3 g, 61%).

Provenance & Evidence