Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylamine | HCID 6341 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | PyBroP | HCID 2733179 | — |
| Reactant | HCID 58087848 | HCID 58087848 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58086682 | HCID 58086682 | 33% |
Reaction Steps
To 3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (P-1559, 38.0 mg, 0.090 mmol) in tetrahydrofuran (2.3 mL) was added a solution of ethylamine (2.0 M in tetrahydrofuran, 0.20 mL), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (80.0 mg, 0.17 mmol) and triethylamine (0.30 mL, 2.2 mmol) under an atmosphere of nitrogen. The reaction mixture was stirred overnight at room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 40% ethyl acetate in hexane to give the compound as a white solid (P-1630, 13.2 mg, 33%). MS (ESI) [M−H+]−=449.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07863288B2 |
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| Source dataset | uspto-grants-2011_01 |
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| ORD ID | ord-808799cfcfb14a729c0cc1ac0f1075ab |
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| Source note | uspto-grants-2011_01 |
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