Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 90332963 | HCID 90332963 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 90332417 | HCID 90332417 | 65% |
Reaction Steps
To a suspension of compound 5-bromo-2-cyclopropyl-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (1.5 g, 3.9 mmol) and K2CO3 (1.6 mg, 7.8 mmol) in DMF (15 mL) was added dropwise CH3I (1.1 mg, 7.8 mmol) at 0° C. under N2, and then the mixture was stirred at 80° C. for 2 hours. After concentration in vacuum, the residue was suspended in H2O and extracted with DCM. The combined organic layer was washed with H2O, brine and dried over Na2SO4. The mixture was filtered and concentrated to give the product of compound 5-bromo-2-cyclopropyl-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1 g, yield: 65%). 1H-NMR (400 MHz, CDCl3) δ 7.70 (s, 1H), 6.98 (s, 1H), 5.63 (s, 1H), 3.05 (s, 3H), 2.79 (s, 6H), 2.39˜2.43 (m, 1H), 0.95˜0.97 (m, 2H), 0.89˜0.91 (m, 2H). MS (M+H)+: 401/403.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09242998B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-6155f0d87d5340cabf4bd34016bfab53 |
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| Source note | uspto-grants-2016_01 |
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