Buchwald–Hartwig amination: 1-(Benzenesulfonyl)-3-(2-chloro-5-methylpyrimidin-4-yl)indole → 1-[4-[4-[[4-[1-(Benzenesulfonyl)indol-3-yl]-5-methylpyrimidin-2-yl]amino]-3-methoxyphenyl]piperazin-1-yl]ethanone
57% yield, run at 90 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
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
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