HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 2-[2-(4-Bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Methyl 2-aminopyridine-4-carboxylate | HCID 236984 | — |
| Reactant | 2-(4-Bromo-2-chlorophenoxy)acetic acid | HCID 693157 | — |
| Reactant | PyBOP | HCID 2724699 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[2-(4-Bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester | HCID 24812096 | 56% |
Reaction Steps
To solution of (4-bromo-2-chloro-phenoxyacetic acid (100 mg, 0.378 mmol), 2-amino isonicotinic acid methyl ester (86.42 mg, 0.568 mmol) and DMAP (69.43 mg, 0.568 mmol) in DMF 2 mL was added PyBOP (295 mg, 0.568 mmol) at room temperature. Reaction mixture was stirred at room temperature. Resulting mixture poured onto ice cold water, was diluted by ethyl acetate. The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:9˜4:6) to give 2-[2-(4-bromo-2-chloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.084 g, 56% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394799B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-f6c65c6971ce41d794aeffbb4f7fb94f |
| Source note | uspto-grants-2013_03 |