Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(Trifluoromethoxy)phenylboronic acid | HCID 2734386 | — |
| Reactant | HCID 86690468 | HCID 86690468 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 86690488 | HCID 86690488 | — |
Reaction Steps
A mixture of N-[(2-bromopyridin-4-yl)methyl]-1-methyl-N-(propan-2-yl)-1H-imidazole-4-carboxamide (100 mg), 4-trifluoromethoxyphenylboronic acid (122 mg), tetrakis(triphenylphosphine)palladium (34 mg), potassium carbonate (82 mg), dimethylformamide (1.2 mL) and ethanol (0.4 mL) was stirred under irradiation with microwave while heating at 150° C. for 30 min. After diluting with chloroform, the mixture was washed with water and further extracted with chloroform. The organic phase was separated out, and the solvent was distilled off under reduced pressure. The resulting residue was diluted with ethyl acetate, and a small amount of NH silica gel was added thereto, followed by stirring. The NH silica gel was filtered off, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by HPLC. The resulting residue was dissolved in acetonitrile and water, and 2N hydrochloride was added thereto, followed by lyophilization to afford the title compound (94 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08729271B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-106f0f61b3c84038ae41050860caedac |
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| Source note | uspto-grants-2014_05 |
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