Buchwald–Hartwig amination: Benzene, 4-bromo-1,2-dimethoxy- → tert-butyl (2R)-4-(3,4-dimethoxyphenyl)-2-propan-2-ylpiperazine-1-carboxylate
36% yield, run at 150 °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 | Benzene, 4-bromo-1,2-dimethoxy- | C₈H₉BrO₂ | |
| Reactant | (R)-1-Boc-2-isopropylpiperazine | C₁₂H₂₄N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl | C₂₆H₃₆NP | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-butyl (2R)-4-(3,4-dimethoxyphenyl)-2-propan-2-ylpiperazine-1-carboxylate | C₂₀H₃₂N₂O₄ | 36% |
Conditions
- Temperature
- 150 °C
Yield
- 36% of tert-butyl (2R)-4-(3,4-dimethoxyphenyl)-2-propan-2-ylpiperazine-1-carboxylate.
Procedure
Copied from the source record, unedited
21-Apr-09 08:58:54 +0100 4-bromo-1,2-dimethoxybenzene (0.068 mL, 0.46 mmol), (R)-tert-butyl 2-isopropylpiperazine-1-carboxylate (126 mg, 0.55 mmol) and 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl (11.21 mg, 0.03 mmol) and Sodium tert-butoxide (63.9 mg, 0.64 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (21.09 mg, 0.02 mmol) were suspended in toluene (5 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 20 minutes in the microwave reactor and cooled to RT. LC-MS shows 36% product and 57% SM reaction will be combined with EN02263-47
The source
This record comes from experimental reaction archive (ord-ca7fdadedf3340de8e255025b11294fe). Open the source and check it against what is on this page.
experimental reaction archive record ord-ca7fdadedf3340de8e255025b11294fe 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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