Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 2,5-Difluorobenzenesulfonyl chloride | HCID 2736911 | — |
| Reactant | HCID 66647207 | HCID 66647207 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 46893808 | HCID 46893808 | 66.1% |
Reaction Steps
To 3-(3-amino-2,6-difluoro-benzoyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (28, 100 mg, 0.335 mmol) in 2.7 mL of tetrahydrofuran, 0.24 mL of pyridine was added. 2,5-Difluoro-benzenesulfonyl chloride (29, 107 mg, 0.503 mmol) was added and the solution was stirred at room temperature for 48 hours. The reaction mixture was poured into 1 M aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under vacuum. The crude material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and the solvent removed under reduced pressure to provide the desired compound (P-0004, 105 mg). MS(ESI)[M+H+]+=475.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08901301B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-d463254c9ca34bde93149cdac11afece |
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| Source note | uspto-grants-2014_12 |
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