Buchwald–Hartwig amination, record ord-9030d498cd864647879671340ebf8182
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 | 5-Bromo-2-methoxybenzonitrile | C₈H₆BrNO | |
| Reactant | (R)-2-(tert-butyldimethylsilyloxy)propan-1-amine | C₉H₂₃NOSi | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | (R)-5-(2-(tert-butyldimethylsilyloxy)propylamino)-2-methoxybenzonitrile | C₁₇H₂₈N₂O₂Si | 20.58% |
Conditions
- Temperature
- 120 °C
Yield
- 21% of (R)-5-(2-(tert-butyldimethylsilyloxy)propylamino)-2-methoxybenzonitrile.
Procedure
Copied from the source record, unedited
Reaction carried PdOAc2 (0.476 g, 2.12 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (1.012 g, 2.12 mmol) were added in one portion to a degassed solution of 5-bromo-2-methoxybenzonitrile (4.50 g, 21.22 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (4.82 g, 25.47 mmol) and cesium carbonate (10.37 g, 31.83 mmol) in toluene (100 mL) at 20°C in a microwave vial. The microwave vial was sealed and the reaction was heated to 120 °C for 12 hours in the microwave reactor and cooled to RT. The reaction mixture was diluted with EtOAc (100 mL) and water (100 mL). The biphasic mixture was filtered through celite. The organic layer was separated and washed sequentially with water (100 mL) and saturated brine (100 mL). The organic layer was filtered and dried over Na2SO
The source
This record comes from experimental reaction archive (ord-9030d498cd864647879671340ebf8182). Open the source and check it against what is on this page.
experimental reaction archive record ord-9030d498cd864647879671340ebf8182 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.