Potassium Carbonate → HCID 59609504, compound

Participants

Reaction Steps

As in Example 4,3-(3,5-dibromophenyl)-1-(pyridin-2-yl)-propenone was synthesized from 3,5-dibromobenzaldehyde and 2-acetylpyridine, and further subjected to a reaction with [2-(6-bromopyridin-2-yl)oxoethyl]pyridinium iodide to synthesize 6-bromo-4′-(3,5-dibromophenyl)-[2,2′;6′,2″]terpyridine. This compound was further subjected to a reaction with 5H-pyrido[4,3-b]indole to synthesize 4′-(3,5-dibromophenyl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine. To 5.1 g of the resulting 4′-(3,5-dibromophenyl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine were added 2.1 g of phenylboronic acid, 0.5 g of tetrakis(triphenylphosphine)palladium, 20 mL of a 2 M aqueous potassium carbonate solution, 72 mL of toluene, and 18 mL of ethanol, followed by heating with reflux while stirring for 12 hours. After cooling to room temperature, the precipitate was collected by filtration. To the precipitate, 80 mL of chloroform was added and insoluble matter was removed by filtration. The filtrate was concentrated under a reduced pressure to obtain a crude product. The crude product was purified by column chromatography (carrier: NH silica gel, eluent: toluene) and then recrystallized using o-dichlorobenzene. Thus, 2.1 g (yield, 41%) of 6-(5H-pyrido[4,3-b]indol-5-yl)-4′-[1,1′;3′,1″]terphenyl-5′-yl-[2,2′;6′,2″]terpyridine (Compound 136) was obtained as a white powder.

Provenance & Evidence