Buchwald–Hartwig amination, record ord-1fab0d514b4b411abf5f6ef0f4a2b24e
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-Bromo-3-methylpyridine | C₆H₆BrN | |
| 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 | tert-butyl (3R)-3-[(3-methylpyridin-2-yl)amino]piperidine-1-carboxylate | C₁₆H₂₅N₃O₂ | 82.37% |
Conditions
- Temperature
- 115 °C
Yield
- 82% of tert-butyl (3R)-3-[(3-methylpyridin-2-yl)amino]piperidine-1-carboxylate.
Procedure
Copied from the source record, unedited
Test reaction using the conditions which were shown to work in EN07957-76 2016-02-26 14:30; Pd2(DBA)3 (14 mg) and BINAP (19 mg) was stirred in toluene (2.5 ml). 14:35; 2-bromo-3-methylpyridine (344 mg), sodium t-butoxide (334 mg), and the amine (526 mg) was added to the mixture. 14:40; Heating at 115 °C. 15:10; 81% product. 15:40; 81% product, No further progress was observed, probably because of lack of amine 15:50; Another 0.4 ml amine was added to the mixture. 16:15; No further progress by HPLC, reaction terminated. 50 microlitres of the mixture was evaporated and the residue was dissolved in methanol-d4 and 1H NMR was recorded. By 1H NMR the starting pyridine was consumed completely, as opposed to the HPLC-MS which indicated 16% starting material. 2016-02-29 10:35; Purificati
The source
This record comes from experimental reaction archive (ord-1fab0d514b4b411abf5f6ef0f4a2b24e). Open the source and check it against what is on this page.
experimental reaction archive record ord-1fab0d514b4b411abf5f6ef0f4a2b24e 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.