Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Reactant | HCID 131732284 | HCID 131732284 | — |
| Catalyst | copper(I) bromide | HCID 24593 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 131732285 | HCID 131732285 | 36% |
Reaction Steps
Sodium nitrite (0.034 g, 0.49 mmol) was added to a 0° C. solution of 6-(N-(4-amino-3,5-difluorophenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (0.235 g, 0.444 mmol) in Acetonitrile (3 ml) and aq HBr (48%) (3 mL). The reaction mixture was stirred for 30 min at 0° C. and copper (I) bromide (0.076 g, 0.53 mmol) was added. The reaction mixture was stirred at 90° C. for 2 h and diluted with EtOAc and water. The organic layer was washed with brine, dried (Na2SO4), filtered, evaporated and purified by silica gel chromatography (0-50% EtOAc/hexanes) to afford the title compound (0.094 g, 36%) as a white foam. LCMS (m/z, ES+)=593.2, 595.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08927593B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-355ac1cc451b4196b4faf9ea6bd372f2 |
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| Source note | uspto-grants-2015_01 |
|---|