Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Nitropyridin-2-ylamine | HCID 77887 | — |
| Reactant | HCID 86698898 | HCID 86698898 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 67974983 | HCID 67974983 | 37% |
Reaction Steps
A reaction mixture of 4-(2-((2,8-dichloroquinolin-5-yl)oxy)ethyl)morpholine (81.5 mg, 0.25 mmol, 1 eq.), 2-amino-3-nitropyridine (41.3 mg, 0.27 mmol, 1.1 eq.), Pd(OAc)2 (1.1 mg, 2 mol %), XantPhos (2.9 mg, 2 mol %) and Cs2CO3 (228 mg, 2.8 eq.)) in t-BuOH (1 mL) was heated at 90° C. and stirred for 20 hours. The reaction mixture was then concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic phase was washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford 8-chloro-N-(4-methyl-3-nitropyridin-2-yl)-5-(2-morpholinoethoxy)quinolin-2-amine (41 mg, 37%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09061999B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-956d828eb3994b5b9f1cb0592873614f |
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| Source note | uspto-grants-2015_06 |
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