HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 5-bromo-3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | N,O-Dimethylhydroxylamine | HCID 14232 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 5-Bromo-3-fluoropyridine-2-carboxylic acid | HCID 21075872 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-bromo-3-fluoro-N-methoxy-N-methylpyridine-2-carboxamide | HCID 21075869 | — |
Reaction Steps
5-Bromo-3-fluoropicolinic acid (1.4 g, 6.5 mmol), N,O-dimethylhydroxylamine.HCl (0.82 g, 8.45 mmol), (2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) (3.2 g, 8.45 mmol) and triethylamine (2.3 mL, 16.3 mmol) were stirred in DMF (30 mL) at room temperature for 1 d. EtOAc and sat. aq. Na2CO3 solution was added and the aqueous phase extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography using silica gel and eluting with 20-80% EtOAc in isohexane to afford 5-bromo-3-fluoro-N-methoxy-N-methylpicolinamide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08975406B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-df5bd44246d84c3a9b430adaa880ce09 |
| Source note | uspto-grants-2015_03 |