Potassium Carbonate → HCID 71285035, compound

Participants

Reaction Conditions

Reaction Steps

To a vial was added tert-butyl 8-bromo-3,4-dihydropyrazino[1,2-a]indole-2(1H)-carboxylate (0.318 g, 0.9 mmol), bis(pinacolato)diboron (0.3 g, 1.2 mmol), potassium acetate (0.27 g, 2.7 mmol), and Pd(dppf)Cl2 (26 mg, 4 mol %). The vial was evacuated and back filled with argon. Dioxane (3 mL) was added, the vial was sealed under argon and heated to 120° C. for 18 h. The reaction mixture was then cooled to room temperature and methyl 6-chloro-5-ethyl-2-methoxynicotinate (0.23 g, 1.0 mmol) was added along with K2CO3 (0.38 g, 2.7 mmol) and H2O (300 μL). The vial was sealed again under argon and heated to 120° C. for a further 12 h. The reaction mixture was then cooled to room temperature and diluted with H2O (20 mL). The aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was purified on silica gel (1:1 hexanes/EtOAc) to afford the title compound as a clear oil (0.12 g, 30%).

Provenance & Evidence