2-Naphthalenecarboxaldehyde → HCID 59609565, compound

Participants

Reaction Conditions

Reaction Steps

As in Example 1,3-(naphthalen-2-yl)-1-(pyridin-4-yl)propenone was synthesized from 2-naphthaldehyde and 4-acetylpyridine, and further subjected to a reaction with [2-(6-bromopyridin-2-yl)oxoethyl]pyridinium iodide to synthesize 6-bromo-4′-(naphthalen-2-yl)-[2,2′;6′,4″]terpyridine. To 5.0 g of the resulting 6 bromo-4′-(naphthalen-2-yl)-[2,2′;6′,4″]terpyridine were added 1.9 g of 5H-pyrido[4,3-b]indole, 0.4 g of a copper powder, 4.7 g of potassium carbonate, 0.4 mL of dimethyl sulfoxide, and 22 mL of o-dichlorobenzene, followed by heating and stirring at 140° C. for 5.5 hours. After cooling to room temperature, 800 mL of chloroform was added thereto to remove an insoluble matter by filtration, and the filtrate was concentrated under a reduced pressure to obtain a crude product. The crude product was dissolved in chloroform and subjected to adsorptive purification with NH silica gel and then to recrystallization using o-dichlorobenzene. Thus, 5.1 g (yield, 85%) of 4′-(naphthalen-2-yl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,4″]terpyridine (Compound 132) was obtained as a white powder.

Provenance & Evidence