HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 60205543, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Bis(2-oxo-3-oxazolidinyl)phosphinic chloride | HCID 152842 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | 2,2-Difluorocyclopropane-1-carboxylic acid | HCID 2782823 | — |
| Reactant | 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine | HCID 60205276 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 60205543 | HCID 60205543 | 54.4% |
Reaction Steps
A mixture of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.869 mmol; Example 1, Step H), 2,2-difluorocyclopropanecarboxylic acid (212 mg, 1.74 mmol), and triethylamine (606 μL, 4.35 mmol) in CH2Cl2 (5 mL) at room temperature was treated with BOP-Cl (162 mg, 1.74 mmol). The mixture was stirred at room temperature for 18 hours. 2M LiOH.H2O (3 mL) was then added to the mixture and stirred for 30 minutes. Water (10 mL) was added, and the formed solid was filtered, washed with additional water (3×5 mL), and dried to provide N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,2-difluorocyclopropanecarboxamide (158 mg, 54% yield) as a solid. LCMS (APCI+) m/z 334, 336 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08758830B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-c0d07996066e4b33968ece2fec944175 |
| Source note | uspto-grants-2014_06 |