HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-bromo-N-[1-(trifluoromethyl)cyclopropyl]pyridine-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 5-Bromopyridine-2-carboxylic acid | HCID 608544 | — |
| Reactant | 1-(Trifluoromethyl)cyclopropanamine | HCID 11651197 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-bromo-N-[1-(trifluoromethyl)cyclopropyl]pyridine-2-carboxamide | HCID 70935263 | 54.2% |
Reaction Steps
A mixture of 5-bromopyridine-2-carboxylic acid (150 mg, 0.74 mmol), 1-(trifluoromethyl)cyclopropanamine (93 mg, 0.74 mmol) (Oakwood, Cat. #: 038175), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (345 mg, 0.780 mmol) and triethylamine (310 μL, 2.2 mmol) in methylene chloride (1 mL) was stirred at room temperature for 3 h. The mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with methanol in dichloromethylene (0-5%) to afford the desired product (124 mg). LCMS (M+H)+: m/z=309.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08691807B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-e99f395b882141ce8493f7dc00b8b72e |
| Source note | uspto-grants-2014_04 |