Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tributylamine | HCID 7622 | — |
| Reactant | 1-Hexene | HCID 11597 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | HCID 22508742 | HCID 22508742 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 53757548 | HCID 53757548 | 90.5% |
Reaction Steps
A mixture of 1-(2-chloro-4-iodobenzyl)-6-(ethoxycarbonyl)-2-methylbenzimidazole (1.21 g), 1-hexene (1.12 g), palladium acetate (II) (0.09 g), triphenylphosphine (0.21 g), tri-n-butylamine (1.49 g), and N,N-dimethylformamide (15 ml) was stirred overnight at 60° C. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluate: hexane/ethyl acetate=1/2) to obtain 1-(2-chloro-4-(1-hexen-1-yl)benzyl)-6-(ethoxycarbonyl)-2-methyl-benzimidazole (0.99 g). In accordance with the method of Production Example 5, this product was immediately converted to the desired compound (0.64 g) containing about 10% of 6-carboxy-1-(2-chloro-4-(1-hexen-2-yl)benzyl)-2-methyl-benzimidazole. This compound 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-de86ec98496942e2ae70f5bca4b738e2 |
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| Source note | uspto-grants-2002_07 |
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