HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Water → 4-[5-bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-N-methyl-benzamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Sodium Carbonate | HCID 10340 | — |
| Edukt | 4-(Methylcarbamoyl)benzeneboronic acid | HCID 2773526 | — |
| Edukt | 5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 49759066 | — |
| Katalysator | HCID 178418476 | HCID 178418476 | — |
| Lösungsmittel | Acetonitrile | HCID 6342 | — |
| Produkt | 4-[5-bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-N-methyl-benzamide | HCID 66778933 | 121% |
Reaktionsschritte
5-Bromo-3-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (350 mg, 0.73 mmol), 4-(N-methylaminocarbonyl)phenylboronic acid (160 mg, 0.88 mmol) and dichlorobis(triphenylphosphine)palladium (II) (52 mg, 0.073 mmol) were combined in CH3CN (10 ml) and 1 M Na2CO3 (10 ml) and stirred at 60° C. for 5 hrs. Water was added and the mixture was extracted with DCM, combined organic phases were dried and evaporated to yield 428 mg (121%) of the title compound. 1H NMR (CDCl3, 300 MHz): δ 8.50 (d, J=1.3 Hz, 1H), 8.20 (d, J=1.2 Hz, 1H), 8.09 (d, J=5.1 Hz, 2H), 7.94 (s, 1H), 7.87 (d, J=5.1, 2H), 7.61 (d, J=5.0 Hz, 2H), 7.31 (d, J=5.0 Hz, 2H), 6.21 (bd, J=2.5 Hz, 1H), 3.06, (d, J=2.9 Hz, 3H), 2.39 (s, 3H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08846909B2 |
| Quelldatensatz | uspto-grants-2014_09 |
| ORD ID | ord-7bca94649fc947189c47d1c8a65482e5 |
| Quellennotiz | uspto-grants-2014_09 |