Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (Naphthalen-2-yl)boronic acid | HCID 2734375 | — |
| Reactant | HCID 68625661 | HCID 68625661 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | HCID 59609503 | HCID 59609503 | 71.5% |
Reaction Steps
To 4.6 g of the 4′-(4-bromophenyl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine obtained in Example 4 were added 1.4 g of 2-naphthaleneboronic acid, 0.5 g of tetrakis(triphenylphosphine)palladium, 21 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 6 hours. After cooling to room temperature, a precipitate was collected by filtration. To the precipitate, 200 mL of o-dichlorobenzene was added and insoluble matter was removed by filtration. The filtrate was concentrated under a reduced pressure to obtain a concentrate. The concentrate was dissolved in chloroform and subjected to adsorptive purification with NH silica gel. Thereafter, the filtrate was concentrated under a reduced pressure to obtain a crude product. The crude product was washed with ethyl acetate to obtain 3.5 g (yield, 69%) of 4′-(4-naphthalen-2-yl-phenyl)-6-(5H-pyrido[4,3-b]indol-5-yl)-[2,2′;6′,2″]terpyridine (Compound 134) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08624228B2 |
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| Source dataset | uspto-grants-2014_01 |
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| ORD ID | ord-6c3766933ad047c4b89a361f39fa1757 |
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| Source note | uspto-grants-2014_01 |
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