Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 59654915 | HCID 59654915 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 11211181 | HCID 11211181 | 54.3% |
Reaction Steps
A flask containing 6-bromo-3-(3H-imidazol-4-yl)-4-phenyl-1H-quinolin-2-one (23 mg, 0.063 mmol) (Example 134), K2CO3 (30 mg, 0.22 mmol), methyl iodide (4 μL, 0.063 mmol) and 0.1 mL of DMF was stirred at 25° C. for 3 hrs. The compound was purified by RP-HPLC, eluting with 30-70% CH3CN in 0.1% TFA/H2O over 20 mins to give 13 mg (42%) the title compound as a TFA salt. 1H NMR (400 MHz, CD3OD) δ 8.82 (s, 1H), 7.90 (dd, 1H), 7.70 (d, 1H), 7.62 (m, 3H), 7.34 (m, 3H), 6.60 (s, 1H), 3.92 (s, 3H). Diff Noe, irradiation at 3.92 ppm (N—CH3) enhanced 7.70 ppm (d, 1H, H-8). Mass spectrum (ESI, m/z) calcd. for C19H1BrN3O2 379.0, found 380.0 (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-87070fa5170944d0a8ab2405837af5b5 |
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| Source note | uspto-grants-2008_02 |
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