Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 86728285 | HCID 86728285 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 71295285 | HCID 71295285 | 94.6% |
Reaction Steps
To a solution of ethyl 6-amino-5-bromo-2-(2,4-difluorophenyl)benzofuran-3-carboxylate (310 mg, 0.78 mmol) and pyridine (185 mg, 2.35 mmol) in dichloromethane (10 mL) was added dropwise methanesulfonyl chloride (179 mg, 1.56 mmol) at 0° C., then the mixture was stirred at 25° C. overnight. 10% HCl (aq) was added, then the mixture was extracted with dichloromethane (30 mL*3), dried over Na2SO4, and concentrated to provide ethyl 5-bromo-2-(2,4-difluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylate (350 mg, yield: 94%). 1H-NMR (CDCl3, 400 MHz) δ 8.32 (s, 1H), 7.91 (s, 1H), 7.64˜7.90 (m, 1H), 7.06 (d, J=3.0 Hz, 1H), 7.03 (d, J=3.0 Hz, 1H), 6.88 (s, 1H), 4.38 (q, J=7.2 Hz, 2H), 3.02 (s, 3H), 1.33 (t, J=7.6 Hz, 3H). MS (M+H)+: 474/476.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09265773B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-9ab10053a61448f7a0a6d1f5668426d8 |
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| Source note | uspto-grants-2016_02 |
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