Buchwald–Hartwig amination: 6-Chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine → N-[(1-methylpiperidin-4-yl)methyl]-3-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-amine
63% yield, run at 120 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 6-Chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine | C₁₃H₇ClF₃N₃O | |
| Reactant | 1-Methylpiperidine-4-methylamine | C₇H₁₆N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl | C₂₆H₃₆NP | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | N-[(1-methylpiperidin-4-yl)methyl]-3-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-amine | C₂₀H₂₂F₃N₅O | 62.89% |
Conditions
- Temperature
- 120 °C
Yield
- 63% of N-[(1-methylpiperidin-4-yl)methyl]-3-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-amine.
Procedure
Copied from the source record, unedited
A 500 ml round bottom lfask was charged with a magnetic stir bar, toluene (200 ml), 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (6.55 g, 20.88 mmol), Pd2dba3 (1.912 g, 2.09 mmol), fresh bottle of 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (2.465 g, 6.26 mmol), SODIUM TERT-BUTOXIDE (8.03 g, 83.53 mmol) and (1-methylpiperidin-4-yl)methanamine (4.55 g, 35.50 mmol). The mixture was degassed with N2, the vessel fitted with a reflux condenser, and then placed in an oil bath heated to 120 °C for 16hrs. The mixture was filtered throught a bed of celite, washed with methanol/DCM (3/1), the filtrate was concentrated, the residue was taken into a mixture of water and DCM/Isopropanol (5/1), separated, the water layer was extrated twice with DCM/isopropanol (5/1), the c
The source
This record comes from experimental reaction archive (ord-f81a599dec2242abb77d43e5f1e1fdd1). Open the source and check it against what is on this page.
experimental reaction archive record ord-f81a599dec2242abb77d43e5f1e1fdd1 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
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