Buchwald–Hartwig amination: 2-Chloropyridine → (R)-tert-butyl 3-(pyridin-2-ylamino)piperidine-1-carboxylate
93% yield, run at 110 °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 | 2-Chloropyridine | C₅H₄ClN | |
| Reactant | tert-butyl (3R)-3-aminopiperidine-1-carboxylate | C₁₀H₂₀N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | (R)-tert-butyl 3-(pyridin-2-ylamino)piperidine-1-carboxylate | C₁₅H₂₃N₃O₂ | 93.42% |
Conditions
- Temperature
- 110 °C
Yield
- 93% of (R)-tert-butyl 3-(pyridin-2-ylamino)piperidine-1-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.
- tert-butyl (3R)-3-[(3-methylpyridin-2-yl)amino]piperidine-1-carboxylate82%
- Ethyl 2-(pyridin-2-ylamino)-1,3-oxazole-5-carboxylate38%
- N-pyridin-2-yl-1,3-oxazol-2-amine0%
- 2-Pyridinamine, N-(4-methylphenyl)-91%
- 2-Pyridinamine, N-(4-methylphenyl)-91%
- 2-Pyridinamine, N-(4-methylphenyl)-90%
- 2-Pyridinamine, N-(4-methylphenyl)-89%
- 2-Pyridinamine, N-(4-methylphenyl)-88%
- 2-Pyridinamine, N-(4-methylphenyl)-88%
- 2-Pyridinamine, N-(4-methylphenyl)-87%
- 2-Pyridinamine, N-(4-methylphenyl)-87%
- 2-Pyridinamine, N-(4-methylphenyl)-86%
Procedure
Copied from the source record, unedited
Vial 1) Pd2(dba)3 (0.018 g, 0.02 mmol) and BINAP (0.024 g, 0.04 mmol) were mixed in toluene (1mL) under N2 and stirred at rt for 5min. Vial 2) sodium tert-butoxide (0.999 g, 10.08 mmol), tert-butyl (R)-3-aminopiperidine-1-carboxylate (1.249 g, 6.05 mmol) and 2-chloropyridine (0.477 mL, 5.04 mmol) were mixed in toluene (6mL) under N2. Added the catalyst solution from vial 1. The mixture was heated at 110°C in an oil-bath. LCMS (3h): product, no SM left. The reaction was cooled to rt and the solvent was evaporated. Added EtOAc, washed with water. Purified by column chromatography (using SP4 TM HPFC system, KP-Sil (50g) column, A=heptane, B=EtOAc/2M NH3 in MeOH (9/1), 27mL/fr, (0% B 2CV, 0-30% B 10CV, 30% B 2CV)) to yield tert-butyl (R)-3-(pyridin-2-ylamino)piperidine-1-carboxylate (1.3
The source
This record comes from experimental reaction archive (ord-3016ae12f45142f49e43a15eaa293eb1). Open the source and check it against what is on this page.
experimental reaction archive record ord-3016ae12f45142f49e43a15eaa293eb1 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.
Where to next
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