Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tributylamine | HCID 7622 | — |
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | HCID 22508742 | HCID 22508742 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18467547 | HCID 18467547 | — |
Reaction Steps
A mixture of 1-(2-chloro-4-iodobenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole (0.91 g), phenylacetylene (1.02 g), palladium acetate (II) (0.045 g), triphenylphosphine (0.105 g), tri n-butylamin (1.12 g), copper iodide (I) (0.038 g), and N,N-dimethylformamide (5 ml) was stirred for 1 hour at 70° C. and for 30 minutes at 100° C. After cooling the reaction solution, acetone was added thereto and the solution was filtrated with celite. The filtrate was concentrated and the resulting residue was dissolved in ethyl acetate followed by washing with 1N hydrochloric acid and a 10% aqueous solution of sodium hydroxide. The organic layer was dried and concentrated to obtain crude 1-(2-chloro-4-(phenylethynyl) benzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole. This product was immediately subjected to the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06420409B1 |
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| Source dataset | uspto-grants-2002_07 |
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| ORD ID | ord-50e011a5aa96491a82a30ae912a9de24 |
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| Source note | uspto-grants-2002_07 |
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