HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Diisopropylethylamine → N-(4-(3-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl)-2-fluoro-6-methoxybenzamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | 2-Fluoro-6-methoxybenzoic acid | HCID 2737360 | — |
| Edukt | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Edukt | 4-(3-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine | HCID 21081659 | — |
| Katalysator | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | N-(4-(3-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenyl)-2-fluoro-6-methoxybenzamide | HCID 21081788 | 72% |
Reaktionsschritte
To a stirred solution of 4-(3-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorobenzenamine (400 mg, 0.85 mmol), 2-fluoro-6-methoxybenzoic acid (226 mg, 1.33 mmol), and HATU (641 mg, 1.33 mmol) in DMF (6 mL) was added DIPEA (387 mg, 3 mmol), followed by DMAP (50 mg). The resulting mixture was stirred at rt overnight, diluted with EtOAc, and washed with saturated aq. K2HPO4 solution and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, eluting with 30% EtOAc/CH2Cl2) to give the desired product (370 mg, 72%) as a white solid. LC/MS(ESI+) m/z 605 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07173031B2 |
| Quelldatensatz | uspto-grants-2007_02 |
| ORD ID | ord-23c97d92fec74328a81ddbc9bb70ff80 |
| Quellennotiz | uspto-grants-2007_02 |