Buchwald–Hartwig amination: 2-Bromo-3-chloropyridine → 3-chloro-N-[(3-methyloxetan-3-yl)methyl]pyridin-2-amine
12% yield, run at 115 °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-Bromo-3-chloropyridine | C₅H₃BrClN | |
| Reactant | (3-Methyloxetan-3-yl)methanamine | C₅H₁₁NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 3-chloro-N-[(3-methyloxetan-3-yl)methyl]pyridin-2-amine | C₁₀H₁₃ClN₂O | 12.22% |
Conditions
- Temperature
- 115 °C
Yield
- 12% of 3-chloro-N-[(3-methyloxetan-3-yl)methyl]pyridin-2-amine.
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
In a 5 MW vial, Pd2((dba)3 (7.23 mg, 7.90 µmol), 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (9.71 mg, 0.02 mmol), sodium 2-methylpropan-2-olate (174 mg, 1.81 mmol), (3-methyloxetan-3-yl)methanamine (126 mg, 1.25 mmol) and 2-bromo-3-chloropyridine (200 mg, 1.04 mmol) mixed in toluene (2 mL) to give a brown suspension. The mixture was degassed with N2 bubbling for 5 min, then the vial was capped and the reaction stirred at 115°C in an oil-bath for 1h then to rt for 2h. LC-MS: 61% product, 28% sm left. The reaction was cooled to rt and the solvent was evaporated. The residue was purified by automated flash chromatography on a 25g column. A gradient from 5% to 50% of EtOAc in heptane over 15CV was used as mobile phase. The product was collected using the wavelength 315 nm, rele
The source
This record comes from experimental reaction archive (ord-a5d4f788c47d4d46a04a4c8af6024836). Open the source and check it against what is on this page.
experimental reaction archive record ord-a5d4f788c47d4d46a04a4c8af6024836 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.