Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 2-Chlorophenylboronic acid | HCID 2734322 | — |
| Reactant | HCID 178418785 | HCID 178418785 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67409554 | HCID 67409554 | — |
Reaction Steps
200 mg (1.59 mmol) of methyl 1H-imidazole-4-carboxylate, 496 mg (3.17 mmol) of 2-chloro-phenylboronic acid, 100 mg of 3 Å molecular sieve and 432 mg (2.28 mmol) of copper(II) acetate were initially charged in 2 ml of dichloromethane, and 256 μl (3.17 mmol) of pyridine were added. The mixture was stirred at RT for 20 h. For work-up, the mixture was filtered through a little kieselguhr, the filter residue was rinsed with about 15 ml of ethyl acetate and the combined filtrates were washed with 5 ml of water. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1→1:1→1:3). This gave 55 mg (13% of theory) of the target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09187466B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-c2b3efa86a3041afa6a8d013e6684455 |
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| Source note | uspto-grants-2015_11 |
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