Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | PyBOP | HCID 2724699 | — |
| Reactant | HCID 57736461 | HCID 57736461 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57736412 | HCID 57736412 | 76.1% |
Reaction Steps
To a solution of 4-methyl-5-[(phenylsulfonyl)(2,3,6-trifluorophenyl)methyl]pyridine-2-carboxylic acid (300 mg, 0.71 mmol) in N,N-dimethylformamide (6 ml), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (556 mg, 1.07 mmol), benzotriazol-1-ol (144 mg, 1.07 mmol), ammonium chloride (76 mg, 1.42 mmol), and N-ethyldiisopropylamine (0.5 ml, 2.85 mmol) were added in an Argon atmosphere at room temperature. After stirring for 3 hours at room temperature, ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate, and then was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, subsequently the filtrate was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether, and then was collected by filtration, to obtain the title compound (227 mg, 0.54 mmol, 76%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08114886B2 |
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| Source dataset | uspto-grants-2012_02 |
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| ORD ID | ord-d1ac3bd8eaaa4033b8908b2e17d35840 |
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| Source note | uspto-grants-2012_02 |
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