Buchwald–Hartwig amination, record ord-e759d69f11ae4651a16a93e70cd9c7e3
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 | 3-(2,5-Dichloropyrimidin-4-yl)-8-fluoroimidazo[1,2-a]pyridine | C₁₁H₅Cl₂FN₄ | |
| Reactant | Tert-butyl 2-((4-amino-3-methoxyphenyl)(methyl)amino)acetate | C₁₄H₂₂N₂O₃ | |
| Reagent | Potassium Phosphate, Tribasic | K₃O₄P | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Tert-butyl 2-((4-(5-chloro-4-(8-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxyphenyl)(methyl)amino)acetate | C₂₅H₂₆ClFN₆O₃ | 43.05% |
Conditions
- Temperature
- 100 °C
Yield
- 43% of Tert-butyl 2-((4-(5-chloro-4-(8-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-ylamino)-3-methoxyphenyl)(methyl)amino)acetate.
Procedure
Copied from the source record, unedited
A microwave tube was charged with diacetoxypalladium (11.18 mg, 0.05 mmol), potassium phosphate (529 mg, 2.49 mmol),2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (62.0 mg, 0.10 mmol), 3-(2,5-dichloropyrimidin-4-yl)-8-fluoroimidazo[1,2-a]pyridine (282 mg, 1.00 mmol) purged with nitrogen. Dioxane (4.5 ml) was added followed by tert-butyl 2-((4-amino-3-methoxyphenyl)(methyl)amino)acetate (292 mg, 1.10 mmol). The resulting suspension was purged again and was heated at 100 °C for 1h30. After cooling, the mixture was filtered through a pad of Dicalite speed plus and washed with dichloromethane. The solvent were evaporated. PBO-01970-51-01 The crude product was purified by flash chromatography on silica gel (Merck cartridge SVF D26 - SI60 15-40µm - 30g) eluting with 0 up to 50% EtOAc in petroleum
The source
This record comes from experimental reaction archive (ord-e759d69f11ae4651a16a93e70cd9c7e3). Open the source and check it against what is on this page.
experimental reaction archive record ord-e759d69f11ae4651a16a93e70cd9c7e3 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.