Buchwald–Hartwig amination: (tert-Butyl) 6-bromonicotinate → Tert-butyl 6-piperidin-1-ylpyridine-3-carboxylate
62% yield, run at 80 °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 | (tert-Butyl) 6-bromonicotinate | C₁₀H₁₂BrNO₂ | |
| Reactant | Piperidine | C₅H₁₁N | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Tert-butyl 6-piperidin-1-ylpyridine-3-carboxylate | C₁₅H₂₂N₂O₂ | 61.94% |
Conditions
- Temperature
- 80 °C
Yield
- 62% of Tert-butyl 6-piperidin-1-ylpyridine-3-carboxylate.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
In a 100 mL round-bottomed flask was tert-butyl 6-bromonicotinate (516 mg, 2 mmol), piperidine (237 µl, 2.40 mmol), and CESIUM CARBONATE (977 mg, 3.00 mmol) in dioxane (9763 µl) to give a white suspension. The solution was degassed with N2 (g) fo 20 mins. PALLADIUM(II) ACETATE (22.45 mg, 0.10 mmol) and BINAP (62.3 mg, 0.10 mmol) were added under N2 (g) and the reaction was heated to 100 °C. Start Time: 01-Jul-10 1:10:32 PM -0400. The reaction was checked by LC-MS (complete), filtered, rinsed with DCM, concentrated in vacuo. _02 July 2010_ Purification by Iscos (25 g) using 100% Hexanes -> 50% EtOAc in Hexanes afforded a white solid. 325 mg obtained. 1H NMR (300 MHz, DMSO- _d_ 6) d ppm 1.51 - 1.57 (m, 12 H) 1.57 - 1.77 (m, 5 H) 3.58 - 3.74 (m, 4 H) 6.78 - 6.92 (m, 1 H) 7.88 (dd, _J_ =9.1
The source
This record comes from experimental reaction archive (ord-b099625680284510ba7d7318538524ab). Open the source and check it against what is on this page.
experimental reaction archive record ord-b099625680284510ba7d7318538524ab 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.
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