HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitrogen → HCID 68288093, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Methyl-3-aminopyrazole | HCID 137254 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 6-(Aminomethyl)quinoline | HCID 1514384 | — |
| Reactant | 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline | HCID 54775608 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 68288093 | HCID 68288093 | 14% |
Reaction Steps
To a suspension of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (68 mg, 0.2 mmol) (prepared from quinolin-6-ylmethanamine following the procedures of Compound 1) and 1-methyl-1H-pyrazol-3-amine (20 mg, 0.22 mmol) in dioxane (5 mL) were added Cs2CO3 (72 mg, 0.22 mmol) and H2O (0.5 mL). The mixture was degassed and charged with N2 three times, then Pd2(dba)3 (0.02 mmol, 18 mg) and xantphos (0.04 mmol, 23 mg) were added. The resulting mixture was stirred at 120° C. under one atmosphere of N2 overnight, then concentrated. The resulting residue was purified by chromatography to afford the title compound (10 mg). MS (m/z): 358 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08507487B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-2ca5799253f04d14958c0aae1f02f2c6 |
| Source note | uspto-grants-2013_08 |