Buchwald–Hartwig amination, record ord-59e34daf62ce45d3ab308432983c78e6
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 | 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one | C₉H₈BrNO | |
| Reactant | Benzylamine | C₇H₉N | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Dimethylformamide | C₃H₇NO | |
| Product | 6-benzylamino-3,4-dihydro-2H-isoquinolin-1-one | C₁₆H₁₆N₂O | 0% |
Conditions
- Temperature
- 130 °C
Yield
- 0% of 6-benzylamino-3,4-dihydro-2H-isoquinolin-1-one.
Procedure
Copied from the source record, unedited
In a 5 mL sealed MW* test tube was 6-bromo-3,4-dihydroisoquinolin-1(2H)-one (50 mg, 0.22 mmol), phenylmethanamine (97 µl, 0.88 mmol), BINAP (6.89 mg, 0.01 mmol) and palladium(II) acetate (2.483 mg, 0.01 mmol) in DMF (500 mL) combined to give a tan suspension. potassium tert-butoxide (24.82 mg, 0.22 mmol) was then added last. Placed test tube onto Smith MW* platform. Heated reaction to 130°C for 4 minutes. Reaction know has a heavy black ppt present. Took LCMS - there is some product (~15%) beginning to form. Placed sealed test tube in heated (130°C) oil bath overnight. Took LCMS - all SM is consumed with a moderate product peak in evidence. Transferred reaction to separatory funnel. Partitioned reaction with EtOAc (40 ml) and water (25 ml). Separated off aq layer. Washed with sat NaCl. The
The source
This record comes from experimental reaction archive (ord-59e34daf62ce45d3ab308432983c78e6). Open the source and check it against what is on this page.
experimental reaction archive record ord-59e34daf62ce45d3ab308432983c78e6 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.