Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Bromo-5-(trifluoromethyl)benzenamine | HCID 67989 | — |
| Reactant | Isonicotinoyl chloride hydrochloride | HCID 12262826 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 23149635 | HCID 23149635 | 44.8% |
Reaction Steps
Isonicotinoyl chloride hydrochloride (427 mg, 2.39 mmol, commercially available product) and triethylamine (410 μl, 2.94 mmol) were sequentially added at 0° C. to a dichloromethane (5 ml) solution of 2-bromo-5-(trifluoromethyl)aniline (480 mg, 2.00 mmol; commercially available product). The resulting mixture was warmed to room temperature and stirred for 24 hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by recrystallization (ethyl acetate). Thus, N-[2-bromo-5-(trifluoromethyl)phenyl]isonicotinamide (GIF-0612) (308 mg, 44.8%) was yielded as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08338362B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-bd2708fc147e45459f594c4b5e68f5a2 |
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| Source note | uspto-grants-2012_12 |
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