HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 5-{3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyridine-2-carboxylic acid ethylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | 5-(3-{[2,6-difluoro-3-(propane-1-sulfonylamino)-phenyl]-hydroxy-methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylic acid ethylamide | HCID 59569614 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-{3-[2,6-difluoro-3-(propane-1-sulfonylamino)-benzoyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyridine-2-carboxylic acid ethylamide | HCID 49779382 | 61.7% |
Reaction Steps
To 5-(3-{[2,6-difluoro-3-(propane-1-sulfonylamino)-phenyl]-hydroxy-methyl}-1H-pyrrolo[2,3-b]pyridin-5-yl)-pyridine-2-carboxylic acid ethylamide (73, 50 mg, 0.094 mmol) dissolved in 0.76 mL of tetrahydrofuran, Dess-Martin periodinane (48 mg, 0.113 mmol) was added, followed by 1 mL of dimethylformamide. The reaction was allowed to stir at room temperature for 1 hour, then quenched with water and the aqueous layer extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting residue was purified by silica gel column chromatography to provide the desired compound (P-2151, 30.6 mg). MS (ESI) [M+H+]+=528.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08198273B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-a1f6fbe4d4984609bfc5165c30f0a787 |
| Source note | uspto-grants-2012_06 |