Buchwald–Hartwig amination, record ord-d7f47b4e3d2047bbb6f27fb595bc1873
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 | 2-Bromopyridine | C₅H₄BrN | |
| Reactant | 7-Azaspiro[3.5]nonan-2-yl-(4-cyclobutylpiperazin-1-yl)methanone | C₁₇H₂₉N₃O | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | (4-Cyclobutylpiperazin-1-yl)-(7-pyridin-2-yl-7-azaspiro[3.5]nonan-2-yl)methanone | C₂₂H₃₂N₄O | 42.78% |
Conditions
- Temperature
- 110 °C
Yield
- 43% of (4-Cyclobutylpiperazin-1-yl)-(7-pyridin-2-yl-7-azaspiro[3.5]nonan-2-yl)methanone.
Procedure
Copied from the source record, unedited
cesium carbonate (123 mg, 0.38 mmol) was added to a solution of (4-cyclobutylpiperazin-1-yl)(7-azaspiro[3.5]nonan-2-yl)methanone (100 mg, 0.34 mmol), PdOAc2 (7.70 mg, 0.03 mmol), BINAP (42.7 mg, 0.07 mmol) and 2-bromopyridine (56.9 mg, 0.36 mmol) in toluene (2 mL). The reaction mixture was heated to 110°C for 18hrs. The room temperature cooled down mixture was filtered over celite. The solvent was concentrated. The product was purified by preparative HPLC using a low pH shallow gradient method (Mobile phase: 20-40% B; A: H2O with 0.05% TFA , B: CH3CN, 25 min. run) on Luna 15 m, C8 (2), 21.2x250 mm Phenomenex reverse phase column to provide (4-cyclobutylpiperazin-1-yl)(7-(pyridin-2-yl)-7-azaspiro[3.5]nonan-2-yl)methanone (54.1 mg, 42.8 %) as white solid. 1H NMR (400 MHz, CHLOROFORM- _d_ )
The source
This record comes from experimental reaction archive (ord-d7f47b4e3d2047bbb6f27fb595bc1873). Open the source and check it against what is on this page.
experimental reaction archive record ord-d7f47b4e3d2047bbb6f27fb595bc1873 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.