Buchwald–Hartwig amination, record ord-5c2ff1c91b594cd2a9a708b467e463cc
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 | 62.19% |
Conditions
- Temperature
- 120 °C
Yield
- 62% of (R)-5-(2-(tert-butyldimethylsilyloxy)propylamino)-2-methoxybenzonitrile.
Procedure
Copied from the source record, unedited
Trial reaction for PdOAc2 (0.021 g, 0.09 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.045 g, 0.09 mmol) were added in one portion to a degassed solution of 5-bromo-2-methoxybenzonitrile (0.200 g, 0.94 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (0.214 g, 1.13 mmol) and cesium carbonate (0.461 g, 1.41 mmol) in toluene (10 mL) at 20°C in a microwave vial. The reaction mixture was diluted with EtOAc (20 mL) and water (20 mL). The biphasic mixture was filtered through celite. The organic layer was separated and washed sequentially with water (50 mL) and saturated brine (50 mL). The organic layer was filtered and dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was evaporated and was purified by flash silica chromatog
The source
This record comes from experimental reaction archive (ord-5c2ff1c91b594cd2a9a708b467e463cc). Open the source and check it against what is on this page.
experimental reaction archive record ord-5c2ff1c91b594cd2a9a708b467e463cc 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.