Potassium Carbonate → 6-chloro-5-[2-(morpholin-4-yl)pyrimidin-5-yl]-1H-indole-3-carbaldehyde

Beteiligte Stoffe

Reaktionsschritte

To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (154 mg, 0.584 mmol) in anhydrous 1,4-dioxane (5 mL) and DMF (1 mL) was added N,N-dimethylformiminium chloride (150 mg, 1.17 mmol). The reaction mixture was stirred at room temperature for 20 minutes, then treated with 2 M aqueous potassium carbonate (400 mg, 2.90 mmol), 4-(5-bromopyrimidin-2-yl)morpholine (145 mg, 0.594 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg, 0.068 mmol). The reaction was degassed with nitrogen for 2 minutes and heated to 90° C. for 30 minutes. The cooled reaction mixture was concentrated in vacuo and purified by column chromatography on silica gel (petroleum ether/EtOAc=1:4) to afford 6-chloro-5-[2-(morpholin-4-yl)pyrimidin-5-yl]-1H-indole-3-carbaldehyde (159 mg, 79.4% yield) as an yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.36 (s, 1 H), 10.01 (s, 1 H), 8.55 (s, 2 H), 8.46 (s, 1 H), 8.12 (s, 1 H), 7.79 (s, 1 H), 3.84 (m, 4 H), 3.77 (m, 4 H).

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