Buchwald–Hartwig amination: 5-Bromo-2-methoxybenzonitrile → (R)-5-(2-(tert-butyldimethylsilyloxy)propylamino)-2-methoxybenzonitrile
48% 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-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 | 47.64% |
Conditions
- Temperature
- 120 °C
Yield
- 48% of (R)-5-(2-(tert-butyldimethylsilyloxy)propylamino)-2-methoxybenzonitrile.
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.
Procedure
Copied from the source record, unedited
PdOAc2 (0.529 g, 2.36 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (1.124 g, 2.36 mmol) were added in one portion to a degassed solution of 5-bromo-2-methoxybenzonitrile (5 g, 23.58 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (5.36 g, 28.30 mmol) and cesium carbonate (11.52 g, 35.37 mmol) in toluene (100 mL) at 20°C under nitrogen. The resulting suspension was stirred at 120 °C for 50 hours. The reaction mixture was diluted with EtOAc (150 mL) and water (150 mL) and the biphasic mixture was filtered through celite. The organic layer was separated and washed sequentially with water (150 mL) and saturated brine (150 mL). The organic layer was evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient
The source
This record comes from experimental reaction archive (ord-3a15989581314d86a106f9d713384402). Open the source and check it against what is on this page.
experimental reaction archive record ord-3a15989581314d86a106f9d713384402 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.
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Where to next
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