Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 6-Bromopyridine-3-carbonitrile | HCID 5005718 | — |
| Reactant | Methyl 9H-carbazole-4-carboxylate | HCID 19897888 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67307888 | HCID 67307888 | 64.7% |
Reaction Steps
0.49 g of 2-bromo-5-cyanopyridine, 2.2 g of caesium carbonate, 0.12 g of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene and 0.04 g of palladium acetate are successively added to a solution of 0.40 g of 9H-carbazole-4-carboxylic acid methyl ester, obtained according to stage 2 of Example 1, in 30 ml of dioxane under an inert argon atmosphere. The reaction mixture is refluxed for 2 hours, and then cooled, filtered and concentrated under reduced pressure. The residue is purified by silica gel chromatography (15-40 μm), elution being carried out with a mixture of petroleum ether and dichloromethane (60/40 by volume), so as to give 376 mg of 9-(5-cyanopyridin-2-yl)-9H-carbazole-4-carboxylic acid methyl ester in the form of a yellow powder, the characteristics of which are the following:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08309721B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-15f5ffc788784f21b2bb244ef3bdd187 |
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| Source note | uspto-grants-2012_11 |
|---|