Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Methylcarbamoyl)benzeneboronic acid | HCID 2773526 | — |
| Reactant | 2-Bromo-4-chloro-5-nitrotoluene | HCID 3084778 | — |
| Solvent | HCID 21916312 | HCID 21916312 | — |
| Product | HCID 67155404 | HCID 67155404 | — |
Reaction Steps
To a mixture of the crude product from Step 1 (400 mg, 1.6 mmol), 4-(methylcarbamoyl)phenylboronic acid (286 mg, 1.6 mmol) and sodium carbonate (340 mg, 3.2 mmol) in dimethoxylethane/water (12/4 mL), is added palladium tetrakis(triphenylphospine) (93 mg, 5% mmol). The mixture is purged with N2 for 3 min, then sealed and heated at 90° C. for 3 h. The mixture is cooled, filtered and concentrated. The residue is purified with silica gel chromatography (30% ethyl acetate in DCM) to afford 5′-chloro-N,2′-dimethyl-4′-nitrobiphenyl-4-carboxamide as yellow solid. ESMS m/z 305.1 (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-53ee3becf3c548dabafc4f757bb23a5a |
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| Source note | uspto-grants-2013_05 |
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