HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (S)-N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxypropanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Bis(2-oxo-3-oxazolidinyl)phosphinic chloride | HCID 152842 | — |
| Reactant | (S)-(-)-2-Methoxypropionamide | HCID 2733586 | — |
| Reactant | 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine | HCID 60205276 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Product | (S)-N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxypropanamide | HCID 60205368 | 87.5% |
Reaction Steps
5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.5 g, 2.17 mmol; Example 1, Step H), (S)-2-methoxypropanamide (0.471 g, 4.56 mmol), BOP-Cl (1.16 g, 4.56 mmol), and triethylamine (1.51 mL, 10.9 mmol) were placed in DCM (10 mL) and stirred for 18 hours at room temperature, then poured into water, and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated to give the crude product, which was purified by reverse phase chromatography (Biotage SP4, C-18 25M+, 5-95% CH3CN/water) to give (S)-N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methoxypropanamide (0.6 g, 87% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178131B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-ce2de724ed3f4abcb22399c0a6c01cc3 |
| Source note | uspto-grants-2012_05 |