Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Fluorophenylboronic acid | HCID 2734354 | — |
| Reactant | HCID 86656165 | HCID 86656165 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86656167 | HCID 86656167 | 78.6% |
Reaction Steps
To a mixture of 7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (0.15 g, 0.41 mmol) and (2-fluorophenyl)boronic acid (0.069 g, 0.49 mmol) in 1,4-dioxane (2 mL) was added 1 N solution of sodium carbonate (0.065 g, 0.62 mmol) in water (0.62 mL, 34 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.020 mmol). The mixture was heated at 100° C. overnight. After cooling, the mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, and concentrated and purified on silica gel (0-100% EtOAc in Hexane) to give the desired product (100 mg, 78%). LCMS calculated for C18H16FN2O2(M+H)+: m/z=311.1; found: 311.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680108B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-73e13cad9e5d4910a83ef3b5a86d68a2 |
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| Source note | uspto-grants-2014_03 |
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