Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Methylpyridine-4-boronic acid pinacol ester | HCID 16414274 | — |
| Reactant | HCID 86683085 | HCID 86683085 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86683086 | HCID 86683086 | 15% |
Reaction Steps
A suspension of 4-bromo-2-cyclopentyl-6-trifluoromethyl-quinoline-3-carbonitrile (130 mg, 352 μmol), 2-methylpyridine-4-boronic acid pinacol ester (92.6 mg, 423 μmol), cesium carbonate (103 mg, 317 μmol) and tetrakis(triphenylphosphine)palladium (0) (40.7 mg, 35.2 μmol) in DMF (5.2 ml) was heated to 90° C. for 16 h. The reaction mixture was poured on water and extracted with EtOAc. The combined extracts were washed with water and brine, dried with Na2SO4 and evaporated. The remaining solid was purified by column chromatography (silica gel, n-heptane/EtOAc 4:1) to afford the title compound (20 mg, 15%) as off-white solid. MS (ESI): 382.6 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09199938B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-1bac39c5a45a40a4892e15f3932e7f55 |
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| Source note | uspto-grants-2015_12 |
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