Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Bromo-2-fluorobenzeneboronic acid | HCID 2773333 | — |
| Reactant | 2-bromo-5H-pyrrolo[2,3-b]pyrazine | HCID 25067308 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 90313071 | HCID 90313071 | 35% |
Reaction Steps
To a 150 mL screw-cap vessel under nitrogen was added 5-bromo-4,7-diazaindole (1.0 g, 5.05 mmol), 4-bromo-2-fluorophenyl boronic acid (1.33 g, 6.06 mmol), Pd(dppf)Cl2.CH2Cl2 (0.2 g, 0.24 mmol), K2CO3 (2.09 g, 15.2 mmol), 1,4-dioxane (35 mL) and water (13 mL). The mixture was sparged with nitrogen for 10 minutes, the vessel capped and the reaction heated at 95° Celsius for 24 hours. The reaction was then cooled to rt, diluted with ethyl acetate (200 mL) and washed with water (1×100 mL) and brine (1×100 mL). The organic layer was dried with Na2SO4 and evaporated to dryness. The crude product was purified by HPLC giving the title compound (515 mg, 35%). MS (ESI): mass calcd. for C12H7BrFN2, 290.98; m/z found, 292.0 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09079866B2 |
|---|
| Source dataset | uspto-grants-2015_07 |
|---|
| ORD ID | ord-2657e9eb91db4962b6f6a58b16ced0cf |
|---|
| Source note | uspto-grants-2015_07 |
|---|
