1,2-Dimethoxyethane → HCID 86696565, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (100 mg, 0.34 mmol), cesium carbonate (335 mg, 1.03 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (92 mg, 0.38 mmol) were added to a mixture of 1,2-dimethoxyethane (3 mL) and water (1 mL). The mixture was degassed with argon. 1,1′-Bis-(diphenylphosphino)-ferrocene) palladium dichloride (28 mg, 0.03 mmol) was added. The reaction mixture was heated at 150° C. under argon atmosphere for 0.25 h. The reaction mixture was cooled. The mixture was diluted with CH2Cl2 (3 mL) and water was added (3 mL). The layers were separated using a phase separator and the aqueous layer was extracted with CH2Cl2 (2×5 mL). The combined organic layers were concentrated in vacuo. The crude product was purified by flash silica column chromatography (CH2Cl2:MeOH) (1:0 to 9:1) and dried in vacuo to afford the title compound as a yellow solid (93 mg, 72%). ESI-MS m/z: 374 (M+H)+.

Provenance & Evidence