Buchwald–Hartwig amination, record ord-77fa1d8a9ea647299df5929297f3aa17
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-[(5-Bromo-3-methoxy-2-pyridinyl)carbonyl]cyclopropanecarboxylic acid ethyl ester | C₁₃H₁₄BrNO₄ | |
| Reactant | 2-fluoro-N-(2-methylpropyl)-5-(trifluoromethyl)aniline | C₁₁H₁₃F₄N | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | (1S,2S)-2-[(5-{[2-Fluoro-5-(trifluoromethyl)phenyl](2-methylpropyl)amino}-3-methoxypyridin-2-yl)carbonyl]cyclopropanecarboxylic acid | C₂₂H₂₂F₄N₂O₄ | 29.09% |
Conditions
- Temperature
- 110 °C
Yield
- 29% of (1S,2S)-2-[(5-{[2-Fluoro-5-(trifluoromethyl)phenyl](2-methylpropyl)amino}-3-methoxypyridin-2-yl)carbonyl]cyclopropanecarboxylic acid.
Procedure
Copied from the source record, unedited
(allt satsas i Toluen, N2 bubblar) start 09-jun-2014 19:51:32 +0200. LCMS-1 1600 nästa em ser bra ut, hittar inga SM, får svalna - bryter. Späder med 30 ml etoac, filtrerar genom SiO plugg, evap. evap två gånger ur 30 ml THF, LCMS-2 visar P 10-jun-2014 19:15:25 +0200 löser i 20 ml THF, 10 ml MeOH, adderar LiOH(758 mg löst i 20 ml aq) - lösning, rör rt. Kl 1951 kör LCMS-3, ser riktigt bra ut, inga SM kvar ser det ut som. Ser ingen substitution F mot MeO. Kl 20.20 quench med 2 ml HOAc, evap hårt, m=5.0 g - till SSL. 16-jun-2014 11:32:38 +0200 nu fått åter 1.4 g dygt från SSL samt även dess enantiomer. Tar det via pulvret och kör HNMR (3.5 mg i DMSO). Visar rester från upprening, sätter kl 12.07 på indunstaren med fullt vakuum 60 grC badT samt kolsyreis/aceton kylning få förlaget. Går fram
The source
This record comes from experimental reaction archive (ord-77fa1d8a9ea647299df5929297f3aa17). Open the source and check it against what is on this page.
experimental reaction archive record ord-77fa1d8a9ea647299df5929297f3aa17 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.