5-bromo-6-chloro-1H-indole-3-carbaldehyde → 5-{4-[(1-acetylazetidin-3-yl)methoxy]phenyl}-6-chloro-1H-indole-3-carbaldehyde

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a mixture of 1-(3-{[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenoxy]methyl}azetidin-1-yl)ethanone (160 mg, 0.64 mmol), 5-bromo-6-chloro-1H-indole-3-carbaldehyde (165.4 mg, 0.64 mmol) in 2M aqueous potassium carbonate (1.3 mL, 2M), toluene (3 mL) and ethanol (1 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (46 mg, 0.064 mmol). The mixture was degassed with nitrogen for 5 minutes. The mixture was heated to 110° C. and stirred under microwave irradiation for 2 hours. The cooled reaction mixture was extracted with ethyl acetate (10 mL×3). The combined organic layers was dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown residue. The residue was purified by flash column chromatography (petroleum ether/ethyl acetate=20:1 to 3:1) to give 5-{4-[(1-acetylazetidin-3-yl)methoxy]phenyl}-6-chloro-1H-indole-3-carbaldehyde (127 mg, 52%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ 10.01 (s, 1H), 7.60-7.39 (m, 5H), 6.99 (d, 2H), 4.30 (m, 1H), 4.20-4.09 (m, 4H), 3.93 (m, 1H), 3.07 (m, 1H), 1.91 (s, 3H).

Herkunft & Nachweise