Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline | HCID 54775608 | — |
| Reactant | HCID 178514179 | HCID 178514179 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59341976 | HCID 59341976 | — |
Reaction Steps
To a degassed solution of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (1.6 g, 4.69 mmol) in DMF (8 mL), was added Pd(PPh3)4 (0.434 g, 0.375 mmol) and dicyanozinc (0.441 g, 3.75 mmol). The reaction mixture was heated to 127° C. for 4 h. NH4Cl(aq) was added to quench the reaction, followed by EtOAc. The reaction mixture was filtered through celite, washed with saturated NaHCO3 and NH4Cl. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give a crude product, which was purified with Analogix gel silica (Hexanes:EtOAc) to afford the title compound as a light yellow solid. LCMS (method B): [MH]+=288, tR=1.81 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08497368B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-de8c61cde6b44b488eb9b934e2451ecb |
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| Source note | uspto-grants-2013_07 |
|---|