2-Naphthalenecarboxaldehyde → HCID 59609570, compound

Participants

Reaction Conditions

Reaction Steps

As in Example 1,3-(naphthalen-2-yl)-1-(pyridin-3-yl)propenone was synthesized from 2-naphthaldehyde and 3-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′,3″]terpyridine. To 4.4 g of the resulting 6-bromo-4′-(naphthalen-2-yl)-[2,2′;6′,3″]terpyridine were added 1.7 g of 5H-pyrido[4,3-b]indole, 0.3 g of a copper powder, 4.2 g of potassium carbonate, 0.3 mL of dimethyl sulfoxide, and 20 mL of o-dichlorobenzene, followed by heating and stirring at 140° C. for 3 hours. After cooling to room temperature, 50 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, 2.9 g (yield, 55%) of 4′-(naphthalen-2-yl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,3″]terpyridine (Compound 131) was obtained as a white powder.

Provenance & Evidence