Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | Sodium Formate | HCID 2723810 | — |
| Reactant | HCID 61945180 | HCID 61945180 | — |
| Catalyst | Tetraethylammonium Chloride | HCID 5946 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67223823 | HCID 67223823 | 96.3% |
Reaction Steps
To a stirred de-gassed solution of 2-bromo-N-ethyl-N-(2-methyl-allyl)-5-nitro-benzamide (150 mg, 0.46 mmol), tetra-ethylammonium chloride (84 mg, 0.46 mmol), sodium formate (34 mg, 0.50 mmol) and sodium acetate (82 mg, 1.01 mmol) in anhydrous DMF (10 ml) was added palladium(II) acetate (10 mg, 0.046 mmol) and the reaction stirred at 70° C. for 15 hrs. The reaction was cooled to room temperature and filtered through a pad of celite. The solvent was evaporated in vacuo and the resulting residue purified by flash column chromatography (20% ethyl acetate in dichloromethane) to afford the title compound as a yellow solid (110 mg, 96%). HPLC retention time 4.21 min. Mass spectrum (ES+) m/z 249 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399481B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-c7505c8923654caa9491e411e87e844b |
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| Source note | uspto-grants-2013_03 |
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