Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 5-Bromo-6-chloropyridine-3-sulfonyl chloride | HCID 2793626 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 4730021 | HCID 4730021 | — |
Reaction Steps
A cooled (0° C.) solution of 5-bromo-6-chloropyridine-3-sulfonyl chloride (2.00 g; 6.87 mmol) in DCM (20 mL) was treated first with triethylamine (1.06 ml; 7.56 mmol) then with a 5.6 M solution of dimethylamine in EtOH (1.35 ml; 7.56 mmol). The reaction was stirred at 0° C. for 1.5 hours then brine was added and the phases separated. The organic phase was washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to give a residue which was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08273769B2 |
|---|
| Source dataset | uspto-grants-2012_09 |
|---|
| ORD ID | ord-092d46865088455f9af5f748f3df91c6 |
|---|
| Source note | uspto-grants-2012_09 |
|---|