Buchwald–Hartwig amination, record ord-4e29f7f8d4e94f93bbf63ba519f77a6e
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 | N-[(3-bromophenyl)-(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl]-2,6-dimethylbenzamide | C₂₃H₂₇BrN₂O | |
| Reactant | Morpholine | C₄H₉NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 2,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(3-morpholin-4-ylphenyl)methyl]benzamide | C₂₇H₃₅N₃O₂ | 17.99% |
Conditions
- Temperature
- 80 °C
Yield
- 18% of 2,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(3-morpholin-4-ylphenyl)methyl]benzamide.
Procedure
Copied from the source record, unedited
To a suspension of N-((3-bromophenyl)(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl)-2,6-dimethylbenzamide (0.040 g, 0.09 mmol), MORPHOLINE (8.97 µL, 0.10 mmol), BINAP (5.83 mg, 9.36 µmol), and sodium tert-butoxide (0.013 g, 0.14 mmol) in toluene (2 mL) was added palladium(II) acetate (1.051 mg, 4.68 µmol). Nitrogen was passed through the solution for 15 min prior to being heated at 80 °C overnight. Crude LC shows starting material still present. Heated to 110oC for 2 days. Reaqction no longer progressing. Reaction mixture was concentrated in vacuo. Material was diluted with ethyl acetate, filtered thru celite and concentrated in vacuo. Submitted to purification group (52 mg in 1.6 mL DMSO). Received back dried- down fractions. Diluted with DCM, combined and concentrated to afford 2,6-d
The source
This record comes from experimental reaction archive (ord-4e29f7f8d4e94f93bbf63ba519f77a6e). Open the source and check it against what is on this page.
experimental reaction archive record ord-4e29f7f8d4e94f93bbf63ba519f77a6e 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.