Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Reactant | HCID 86683167 | HCID 86683167 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86683168 | HCID 86683168 | 6.8% |
Reaction Steps
8-chloro-2-(2-(quinolin-2-yl)ethyl)pyrido[4,3-d]pyridazin-1(2H)-one (34 mg, 0.101 mmol) was suspended in 2 mL of toluene and 2 mL of methanol under argon. Then, an aqueous solution of sodium carbonate (16.5 mg, 0.15 mmol, 2 M) was added. To the suspension, pyridin-4-boronic acid (13.79 mg, 0.101 mmol) and then tetrakis(triphenylphosphine)palladium(0) (11.67 mg, 10.10 μmol) were added. The reaction mixture was heated in a CEM microwave at 130° C. for 30 min. Water and EA were added. The organic phase was extracted with water, dried (MgSO4) and evaporated. The residue was purified by chromatography (eluent: DCM/methanol) and then recrystallized from EA/diisopropyl ether (1:1) to give 2.6 mg (yield: 6.79%) of the title compound as off-white solid. LC-MS: m/e 380.1 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09273068B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-78be5b013a694fb18497b90dc5e242cb |
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| Source note | uspto-grants-2016_03 |
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