Buchwald–Hartwig amination, record ord-5f9307492f2b4cadaa0478f3250edc2b
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 | 3-Bromoanisole | C₇H₇BrO | |
| Reactant | 2-Methyl-6-(trifluoromethoxy)-1H-indole | C₁₀H₈F₃NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-(Di-tert-butylphosphino)biphenyl | C₂₀H₂₇P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-(3-Methoxyphenyl)-2-methyl-6-(trifluoromethoxy)indole | C₁₇H₁₄F₃NO₂ | 65.49% |
Conditions
- Temperature
- 120 °C
Yield
- 65% of 1-(3-Methoxyphenyl)-2-methyl-6-(trifluoromethoxy)indole.
Procedure
Copied from the source record, unedited
EN04773-51, _Buchwald coupling,_ ** _J. Med. Chem. 2009, page 3846-3854 (exactly same reaction)._** The indole from 4773-41, 1-bromo-3-methoxybenzenee,Pd2(dba)3, JohnPhos and KOtBu were dissolved in toluene. The mixture was warmed at 120 °C for 1h and ~65% conversion was observed on NMR*(see attached NMR). Reaction seems to work fine and assumed better yield than in 4773-50. This could be due to that bromides generally perform better than iodines in the Buchwald coupling. This test reaction was thrown away.
The source
This record comes from experimental reaction archive (ord-5f9307492f2b4cadaa0478f3250edc2b). Open the source and check it against what is on this page.
experimental reaction archive record ord-5f9307492f2b4cadaa0478f3250edc2b 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.