Buchwald–Hartwig amination, record ord-7e36385bcc0c400fb6d43f0b2d0257ca
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-(Benzenesulfonyl)-3-(2-chloro-5-methylpyrimidin-4-yl)indole | C₁₉H₁₄ClN₃O₂S | |
| Reactant | 4-(4-Acetyl-1-piperazinyl)-2-(methyloxy)aniline | C₁₃H₁₉N₃O₂ | |
| 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 | 1-[4-[4-[[4-[1-(Benzenesulfonyl)indol-3-yl]-5-methylpyrimidin-2-yl]amino]-3-methoxyphenyl]piperazin-1-yl]ethanone | C₃₂H₃₂N₆O₄S | 56.61% |
Conditions
- Temperature
- 90 °C
Yield
- 57% of 1-[4-[4-[[4-[1-(Benzenesulfonyl)indol-3-yl]-5-methylpyrimidin-2-yl]amino]-3-methoxyphenyl]piperazin-1-yl]ethanone.
Procedure
Copied from the source record, unedited
Cesium carbonate (2.55 g, 7.82 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.301 g, 0.52 mmol) and diacetoxypalladium (0.058 g, 0.26 mmol) were added to a stirred suspension of 3-(2-chloro-5-methylpyrimidin-4-yl)-1-(phenylsulfonyl)-1H-indole (2 g, 5.21 mmol) and 1-(4-(4-amino-3-methoxyphenyl)piperazin-1-yl)ethanone (1.299 g, 5.21 mmol) in 1,4-dioxane (50 ml). The resulting suspension was degassed with argon and stirred at 90 °C for 2 hours. After cooling, the mixture was filtered through a pad of Dicalite speed plus and washed with dichloromethane. The solvent were evaporated. PBO-01132-93-01 The crude product was purified by flash chromatography on silica gel (Merck cartrige SVP D40 - SI60 16-40µm - 90g) eluting with 0 up to 100% EtOAc in dichloromethane . The 1-(4
The source
This record comes from experimental reaction archive (ord-7e36385bcc0c400fb6d43f0b2d0257ca). Open the source and check it against what is on this page.
experimental reaction archive record ord-7e36385bcc0c400fb6d43f0b2d0257ca 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.