Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 2-Methylthiazole | HCID 77129 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66679602 | HCID 66679602 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66679827 | HCID 66679827 | 65.1% |
Reaction Steps
To a solution of ethyl 1-(5-fluoropyridin-2-yl)-3-iodo-1H-pyrazole-4-carboxylate (0.40 g, 1.11 mmol) in DMF (3.7 mL) were added 2-methyl-1,3-thiazole (0.17 g, 1.66 mmol), palladium(II) acetate (25.0 mg, 0.11 mmol), triphenylphosphine (58.0 mg, 0.22 mmol) and cesium carbonate (0.72 g, 2.22 mmol). The mixture was heated 140° C. in a seal vial. After 2 h, water and saturated aqueous NaHCO3 were added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts was dried over MgSO4, filtered and concentrated. Purification by silica gel chromatography (100% hexanes 50% hexanes/ethyl acetate) gave the title compound (0.24 g). MS 333.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946231B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-a4f13c0f1b9245bc927ff1c779eb8e83 |
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| Source note | uspto-grants-2015_02 |
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