Buchwald–Hartwig amination, record ord-f89f3a46444e42c0973a5acc34e50e60
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 | 1-(Benzyloxy)-3-bromobenzene | C₁₃H₁₁BrO | |
| 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 | 2-Methyl-1-(3-phenylmethoxyphenyl)-6-(trifluoromethoxy)indole | C₂₃H₁₈F₃NO₂ | 62.48% |
Conditions
- Temperature
- 80 °C
Yield
- 62% of 2-Methyl-1-(3-phenylmethoxyphenyl)-6-(trifluoromethoxy)indole.
Procedure
Copied from the source record, unedited
EN04773-54, _Buchwald coupling, toluene and bromide_ The indole from 4773-41, 1-(benzyloxy)-3-bromobenzene,Pd2(dba)3 (5mol%), JohnPhos (10mol%) and KOtBu (1.4eq) were dissolved in toluene. The mixture was warmed at 80 °C for 40 hours.* The reaction was carefully monitored and analysis data from 2h, 4, 16 and 40 h are attached. According to LCMS there were ca 75% conversion to the product. The mixture was washed with water, concentrtaed and purified by silica column (Hep/EtOAc 6:1). The collected fractions contained product (6 g, 62.5% yield) but had some impurity (see TLC and NMR). Nevertheless Friedel crafts acylation was performed without further purifications. See e.g. 4773-56. ### *JohnPhos, pd2(dba)3 and sodium tertbutoxide had been dissolved in toluene and was portionwise added to
The source
This record comes from experimental reaction archive (ord-f89f3a46444e42c0973a5acc34e50e60). Open the source and check it against what is on this page.
experimental reaction archive record ord-f89f3a46444e42c0973a5acc34e50e60 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.