Buchwald–Hartwig amination, record ord-09bc2ed031574d359c24db47dee15c88
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
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 | 35.87% |
Conditions
- Temperature
- 110 °C
Yield
- 36% 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 300 ml round bottom lfask was charged with a magnetic stir bar, toluene (39 ml), 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (1.1 g, 3.51 mmol), Pd2(dba)3 (0.321 g, 0.35 mmol), 2-(DIMETHYLAMINO)-2'-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (0.414 g, 1.05 mmol), SODIUM TERT-BUTOXIDE (1.011 g, 10.52 mmol), and (1-methylpiperidin-4-yl)methanamine (0.674 g, 5.26 mmol). The mixture was degassed with N2, the vessel fitted with a reflux condenser, and then placed in an oil bath heated to 110 °C for 16hrs. The mixture was cooled to r.t, filtered throught a bed of celite, washed with methanol, the filtrate was concentrated, the residue was pre-absorbed onto silca gel (~10g) and purified with ISCO (eluent methanol/DCM (1/3) to afford the title compound N-((1-methylpiperidin-4-yl)methyl)-
The source
This record comes from experimental reaction archive (ord-09bc2ed031574d359c24db47dee15c88). Open the source and check it against what is on this page.
experimental reaction archive record ord-09bc2ed031574d359c24db47dee15c88 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
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.