Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Chloroquinoline | HCID 11928 | — |
| Reactant | HCID 67469066 | HCID 67469066 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58546965 | HCID 58546965 | 63.35% |
Reaction Steps
To a solution of 2-azetidin-3-yl-3-(3-methoxy-phenyl)-pyrazine hydrochloride (138 mg, 0.50 mmol) and 2-chloro-quinoline (84 mg, 0.50 mmol) in DMF (6 mL) was added Cs2CO3 (325 mg, 1.0 mmol). The reaction mixture was stirred at 110° C. overnight. The reaction mixture was diluted with water, extracted with EtOAc (30 mL×2). The combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 40% EtOAc in petroleum ether) to give 2-{3-[3-(3-methoxy-phenyl)-pyrazin-2-yl]-azetidin-1-yl}-8-methyl-quinoline (118 mg, 0.31 mmol, 63.35%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08957073B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-93ef3a46a42f4c869577d3580e512791 |
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| Source note | uspto-grants-2015_02 |
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