Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| Reactant | HCID 58408403 | HCID 58408403 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58408406 | HCID 58408406 | — |
Reaction Steps
A solution of methyl 2-bromo-5-(5-methylpyridin-3-yl)benzoate (2-3, 0.269 g, 0.88 mmol, 1.0 equiv), 1-methylpyrazole-4-boronic acid pinacol ester (0.274 g, 1.32 mmol, 1.5 equiv), 4M Cs2CO3 (0.769 mL, 3.08 mmol, 3.5 equiv) and PdCl2(dppf) (0.064 g, 0.088 mmol, 0.1 equiv) was made in DMF (4.5 mL) and stirred at 130° C. for 35 minutes. The reaction mixture was cooled and partitioned between EtOAc and water. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organics were washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by normal phase column chromatography (0 to 5% MeOH in EtOAc) to afford the product (2-4) as a solid. ESI+ MS [M+H]+ C18H17N3O2O: 308.02 found, 308.36 required.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08399494B2 |
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| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-cace5a3d02744becbeaf2f7653c83987 |
|---|
| Source note | uspto-grants-2013_03 |
|---|
