Buchwald–Hartwig amination: 5-Bromo-2-methoxy-4-(4-methyl-piperazin-1-yl)-phenylamine → N-[5-amino-4-methoxy-2-(4-methyl-1-piperazinyl)phenyl]carbamic acid 1,1-dimethylethyl ester
0% yield, run at 120 °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 | 5-Bromo-2-methoxy-4-(4-methyl-piperazin-1-yl)-phenylamine | C₁₂H₁₈BrN₃O | |
| Reactant | tert-Butyl carbamate | C₅H₁₁NO₂ | |
| 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 | N-[5-amino-4-methoxy-2-(4-methyl-1-piperazinyl)phenyl]carbamic acid 1,1-dimethylethyl ester | C₁₇H₂₈N₄O₃ | 0% |
Conditions
- Temperature
- 120 °C
Yield
- 0% of N-[5-amino-4-methoxy-2-(4-methyl-1-piperazinyl)phenyl]carbamic acid 1,1-dimethylethyl ester.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
- tert-butyl N-(5-chloropyridazin-3-yl)carbamate100%
- tert-butyl N-(3-fluoro-4-formylphenyl)carbamate97%
- tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate26%
- 2-(Tert-butoxycarbonylamino)-6-chloroisonicotinic acid0%
- (4-Hydroxymethyl-6-methyl-pyridine-2-yl)-carbamic acid tert-butyl ester0%
- tert-Butyl (5-fluoro-6-methylpyridin-2-yl)carbamate0%
- 3-(Boc-amino)pyridinenot recorded
- tert-butyl N-(3-fluoro-5-methyl-2-pyridinyl)carbamate26%
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
- 3-(Boc-amino)pyridinenot recorded
Procedure
Copied from the source record, unedited
To a suspension of 5-bromo-2-methoxy-4-(4-methylpiperazin-1-yl)aniline (50 mg, 0.17 mmol) in dioxane (4 mL) was added tert-butyl carbamate (24.39 mg, 0.21 mmol), cesium carbonate (81 mg, 0.25 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (19.27 mg, 0.03 mmol). The resulting suspension was degassed and Palladium(II) acetate (3.74 mg, 0.02 mmol) was added. The mixture was degassed and stirred at 120 °C for 2 hours in the CEM microwave, then allowed to cool to ambient temperature. The reaction was incomplete so further cesium carbonate (81 mg, 0.25 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (19.27 mg, 0.03 mmol) and diacetoxyzinc (30.6 mg, 0.17 mmol) were added and the mixture was degassed. Further Palladium(II) acetate (3.74 mg, 0.02 mmol) was added, and the mixture w
The source
This record comes from experimental reaction archive (ord-4ae237ba7d264026afd182c3af660100). Open the source and check it against what is on this page.
experimental reaction archive record ord-4ae237ba7d264026afd182c3af660100 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.
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