Hydrochloric Acid → 6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoic acid

Participants

Reaction Steps

A precursor 9 (methyl 6-((2-ethylhexyl)(phenyl)amino)hexanoate) is obtained by reacting methyl 6-(phenylamino)hexanoate, potassium carbonate, dimethylformamide, and 3-(bromomethyl)heptane. Then, 6-((2-ethylhexyl)(phenyl)amino)hexyl acetate, dimethylformamide, acetic anhydride, 4-cyano-5-dicyanomethylene-3-hydroxy-2-oxo-3-pyrroline disodium salt, and POCl3 are reacted to thus prepare a precursor 10 (methyl6-((4-(4-cyano-5-(dicyanomethyene)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino) hexanoate). Then, methyl 6-((4-(4-cyano-5-(dicyanomethylene)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino) hexanoate, potassium carbonate, dimethylformamide, and 1-bromohexane are reacted to thus produce methyl 6-((4-(4-cyano-5-(dicyanomethyene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoate, which is then reacted with tetrahydrofuran and hydrochloric acid, yielding a precursor 11 (6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino) hexanoic acid). Then, 6-((2-ethylhexyl)(phenyl)amino)hexyl acetate, 6-((4(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol)-3-yl)phenyl)(2-ethylhexyl)amino)hexanoic acid, DPTS, dicyclohexyl carbodiimide, and dichloromethyl are reacted together, thus obtaining a precursor 12 ((9-(6-(tert-butyldimethylsilyloxy)hexyl)-9H-carbazol-3-yl)methyl 6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoate). Then, (9-(6-(tert-butyldimethylsilyloxy)hexyl)-9H-carbazol-3-yl)methyl 6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoate, tetrahydrofuran, and hydrochloric acid are reacted together, yielding a compound 13 ((9-(6-hydrohexyl)-9H-carbazol-3-yl)methyl6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoate). The compound 13 is the dendron compound represented by Formula 6 according to exemplary embodiments.

Provenance & Evidence