HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 5-Bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-Fluoro-N-(2-methylpropyl)aniline | HCID 18543711 | — |
| Reactant | 5-Bromopyridine-2-sulfonyl chloride | HCID 44558097 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-Bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide | HCID 86721873 | 82.9% |
Reaction Steps
To a solution of 5-bromo-pyridine-2-sulfonyl chloride (330 mg, 1.29 mmol) in DCM (10 mL) was added pyridine (208 μL, 2.57 mmol) followed by a solution of (4-fluoro-phenyl)-isobutyl-amine (215 mg, 1.29 mmol) in DCM (10 mL) and the reaction was stirred at room temperature for 16 hours. Water and saturated aqueous NaHCO3 were added and then extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (0-20% EtOAc in cyclohexane) to give 5-bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide (414 mg, 78%). LCMS (m/z, Method A) ES+ 387/389 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09382222B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-1f6acb0786c34e3ca8862c8391a899d9 |
| Source note | uspto-grants-2016_07 |