Buchwald–Hartwig amination, record ord-95b63e9e9ac540bc8fc7f0ffbc5bc6a7
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-(2,5-Dichloropyrimidin-4-yl)-1H-indole | C₁₂H₇Cl₂N₃ | |
| Reactant | 2-Methoxy-5-nitroaniline | C₇H₈N₂O₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 5-chloro-4-(1H-indol-3-yl)-N-(2-methoxy-5-nitrophenyl)pyrimidin-2-amine | C₁₉H₁₄ClN₅O₃ | 0% |
Conditions
- Temperature
- 80 °C
Yield
- 0% of 5-chloro-4-(1H-indol-3-yl)-N-(2-methoxy-5-nitrophenyl)pyrimidin-2-amine.
Procedure
Copied from the source record, unedited
To a stirred solution of 3-(2,5-dichloropyrimidin-4-yl)-1H-indole (100 mg, 0.38 mmol) in dioxane (10 mL) was added 2-methoxy-5-nitroaniline (63.7 mg, 0.38 mmol), cesium carbonate (247 mg, 0.76 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (26.3 mg, 0.05 mmol). The resulting suspension was purged with nitrogen for 5 minutes. diacetoxypalladium (5.10 mg, 0.02 mmol) was added and the mixture was purged with nitrogen for a further 5 minutes, and then heated at 80 °C overnight. UPLC shows di-Cl SM almost completely consumed but no evidence of desired product. Reaction stopped
The source
This record comes from experimental reaction archive (ord-95b63e9e9ac540bc8fc7f0ffbc5bc6a7). Open the source and check it against what is on this page.
experimental reaction archive record ord-95b63e9e9ac540bc8fc7f0ffbc5bc6a7 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.