Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Methylcarbamoyl)benzeneboronic acid | HCID 2773526 | — |
| Reactant | Methyl 2-chloro-4-methoxy-5-nitrobenzoate | HCID 13498833 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68515276 | HCID 68515276 | — |
Reaction Steps
Under nitrogen, the mixture of methyl 2-chloro-4-methoxy-5-nitrobenzoate (292 mg, 1.19 mmol), 4-(methylcarbamoyl)phenylboronic acid (319 mg, 1.79 mmol), dichlorobis(triphenylphosphine)palladium (II) (41 mg, 0.06 mmol) and sodium carbonate (378 mg, 3.57 mmol) in THF (8 mL) and water (2 mL) is heated at 40° C. overnight. The reaction mixture is cooled to room temperature and then partitioned between EtOAc and brine. The organic extracts are dried (Na2SO4), concentrated in vacuo, and purified by silica gel chromatography (EtOAc/Hexanes:1/3) to afford Methyl 5-methoxy-4′-(methylcarbamoyl)-4-nitrobiphenyl-2-carboxylate; ESMS m/z 345.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08440681B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-d9a2fb3f938f47909ffe095859df8ffd |
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| Source note | uspto-grants-2013_05 |
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