Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | HCID 68053719 | HCID 68053719 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 68053718 | HCID 68053718 | — |
Reaction Steps
To a solution of the title compound from Example 1 Step C (0.010 g, 0.038 mmol) in dimethylsulfoxide (0.2 mL) was added a solution of sodium methoxide in methanol (25 wt %, 0.018 mL, 0.078 mmol). The reaction was heated at 165° C. for 1 hour, then cooled to room temperature and purified by flash chromatography (50% ethyl acetate in hexanes, then 100% ethyl acetate) to provide the title compound: LCMS m/z 270.25 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.55 (d, 1.5 Hz, 1 H), 8.43 J=2.7 Hz, 1H), 7.72 (d, J=8.8 Hz, 1 H), 7.66 (dd, J=2.5, 1.8 Hz, 1 H), 6.98 (dd, J=8.8, 2.3 Hz, 1 H), 6.86 (d, J=2.3 Hz, 1 H), 3.95 (s, 3 H), 3.92 (s, 3 H), 3.88 (s, 3 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09382226B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-0a44915d39464d48b993c82e480f202b |
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| Source note | uspto-grants-2016_07 |
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