Toluene → HCID 86698620, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{2-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenoxy]ethyl}morpholine (190 mg, 0.6 mmol) in ethanol (2.4 mL) were added 5-bromo-6-chloro-1H-indole-3-carbaldehyde (187 mg, 0.72 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (45 mg, 0.06 mmol), 2M aqueous potassium carbonate (1.2 mL, 2.4 mmol) and toluene (7 mL). The mixture was degassed with nitrogen for 3 min and heated to 110° C. by microwave irradiation for 1 h. The mixture was concentrated in vacuo to give a residue, which was dissolved with ethyl acetate (50 mL) and washed with brine (2×15 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give a residue, which was purified by flash chromatography to give 6-chloro-5-{4-[2-(morpholin-4-yl)ethoxy]phenyl}-1H-indole-3-carbaldehyde (130 mg, 57%) as a yellow oil.

Provenance & Evidence