Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 135537661 | HCID 135537661 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 135457858 | HCID 135457858 | — |
Reaction Steps
A flask was charged with 6-bromo-3-(3-methyl-isoxazol-5-yl)-4-phenyl-1H-quinolin-2-one (25 mg, 0.066 mmol)(Example 39), phenyl boronic acid (12 mg, 0.098 mmol), Pd(PPh3)4 (7 mg, 10 mol %), 2 M Na2CO3 (0.25 mL), EtOH (0.25 mL), and toluene (0.5 mL) and heated for 2 hrs at 80° C. The reaction was diluted with EtAc (10 mL) and washed with brine (2×10 mL). The organic layer was concentrated and the title product (12 mg, 50%) eluted from a 5 g SPE with 50% EtAc/hex. 1H NMR (400 MHz, CDCl3) δ 11.42 (s, 1H), 7.82 (dd, 1H), 7.20 (m, 12H), 6.52 (s, 1H), 2.24 (s, 3H). Mass spectrum (ESI, m/z) calcd. for C25H18N2O2 378.1, found 379.1 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07326788B2 |
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| Source dataset | uspto-grants-2008_02 |
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| ORD ID | ord-09ac319e5c8e46c286be1da36e0cdc49 |
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| Source note | uspto-grants-2008_02 |
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