Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 8-Hydroxyquinoline | HCID 1923 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 18980104 | HCID 18980104 | — |
| Reactant | 4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one | HCID 67072517 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 25138367 | HCID 25138367 | 32.8% |
Reaction Steps
A mixture of 1-(4-bromophenyl)-1H-1,2,4-triazole (45 mg, 0.20 mmol), 4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one (58 mg, 0.18 mmol), quinolin-8-ol (11 mg, 0.074 mmol, Alfa Aesar), potassium carbonate (33 mg, 0.24 mmol), Copper(I) iodide (14 mg, 0.074 mmol, Alfa Aesar) in DMSO (2 mL) was heated under microwave condition at 160° C. for 30 min. The resulting mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layers were concentrated in vacuo to a green oil. The oil was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2 and then SiO2, 0 to 10% MeOH in CH2Cl2) to yield an off-white solid. The solid was dissolved in DCM and 1 eq of HCl (1N HCl in Et2O) was added, the resulting mixture stirred for 5 min and then concentrated in vacuo to give 27 mg of desired product as an off-white solid. MS (ESI) 458 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08178561B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-0eb43cdaefff48188e430683a70b3bbd |
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| Source note | uspto-grants-2012_05 |
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