Buchwald–Hartwig amination, record ord-ea53d8feb8094f94b89810756f770f19
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-[(4-bromophenyl)-(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl]-2,6-dimethylbenzamide | C₂₃H₂₇BrN₂O | |
| Reactant | Morpholine | C₄H₉NO | |
| Reagent | potassium 2-methylpropan-2-olate | C₄H₉KO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Dimethylformamide | C₃H₇NO | |
| Product | 2,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(4-morpholin-4-ylphenyl)methyl]benzamide | C₂₇H₃₅N₃O₂ | 29.57% |
Conditions
- Temperature
- 130 °C
Yield
- 30% of 2,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(4-morpholin-4-ylphenyl)methyl]benzamide.
Procedure
Copied from the source record, unedited
In a CEM microwave vial was N-((4-bromophenyl)(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl)-2,6-dimethylbenzamide (100 mg, 0.23 mmol), morpholine (0.082 mL, 0.94 mmol), palladium(II) acetate (5.25 mg, 0.02 mmol), BINAP (14.57 mg, 0.02 mmol), and potassium tert-butoxide (52.5 mg, 0.47 mmol) solid and DMF (2 mL) was added. The vial was capped and placed into the microwave at 300 watts, 130 °C for 4 minutes. After reaction completion, the the mixture was concentrated and crude taken up in CH2Cl2 and washed with water and dried (Na2SO4). The material was purified on a 12 gram Isco silica cartridge and eluted with 0% to 5% MeOH 2M NH3/CH2Cl2 to give a light yellowish solid 2,6-dimethyl-N-((7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)(4-morpholinophenyl)methyl)benzamide (30.0 mg, 29.6 %).
The source
This record comes from experimental reaction archive (ord-ea53d8feb8094f94b89810756f770f19). Open the source and check it against what is on this page.
experimental reaction archive record ord-ea53d8feb8094f94b89810756f770f19 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.