Buchwald–Hartwig amination: 2-Bromoanisole → tert-butyl (1S,4S)-5-(2-methoxyphenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
69% yield, run at 105 °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 | 2-Bromoanisole | C₇H₇BrO | |
| Reactant | (1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane | C₁₀H₁₈N₂O₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-butyl (1S,4S)-5-(2-methoxyphenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate | C₁₇H₂₄N₂O₃ | 68.91% |
Conditions
- Temperature
- 105 °C
Yield
- 69% of tert-butyl (1S,4S)-5-(2-methoxyphenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate.
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
TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.046 g, 0.05 mmol) and rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.063 g, 0.10 mmol) were mixed together and evacuated and purged with nitrogen 3 times. toluene (24.91 ml) was added and the resulting mixture heated to 50°C for 10 minutes. In a second reaction vessel was mixed sodium tert-butoxide (0.387 g, 4.03 mmol), (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.500 g, 2.52 mmol), 1-bromo-2-methoxybenzene (0.314 ml, 2.52 mmol) and toluene (24.91 ml). The mixture was evacuated and purged with nitrogen 3 times. The solution of catalyst was added to the reaction mixture and the resulting mixture was heated at 105 °C for 16 hours. The reaction mixture was cooled to RT and filtered through celite and evaporated. The cru
The source
This record comes from experimental reaction archive (ord-0c726797efaf4f12802e1de309e7f336). Open the source and check it against what is on this page.
experimental reaction archive record ord-0c726797efaf4f12802e1de309e7f336 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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
Open in the Reaction Lab
The atom map, the bonds that break and form, and records running the same transformation.
Percent yield calculator
Work out a yield from what you isolated against what the equation allows.
Molecules A–Z
Every named molecule, with its identifiers and sources.