Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Reactant | HCID 131732281 | HCID 131732281 | — |
| Catalyst | copper(I) bromide | HCID 24593 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 131732282 | HCID 131732282 | 73% |
Reaction Steps
Sodium nitrite (0.18 g, 2.55 mmol) was added to a 0° C. solution of 6-(N-(4-amino-3-(trifluoromethyl)phenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (1.3 g, 2.32 mmol) in acetonitrile (14 ml) and aq HBr (48%) (14 mL). The reaction mixture was stirred for 30 min at 0° C. and copper (I) bromide (0.40 g, 2.78 mmol) was added. The reaction mixture was stirred at 60° C. for 1 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 (1.06 g, 73%) as a white foam. LCMS (m/z, ES+)=625.2, 627.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08927593B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-4d7377a8573843b09e1095c81d10467f |
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| Source note | uspto-grants-2015_01 |
|---|