Buchwald–Hartwig amination: 2-Bromo-3-methylpyridine → Cyclohexyl-(3-methyl-pyridin-2-yl)-amine
62% 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-methylpyridine | C₆H₆BrN | |
| Reactant | Cyclohexylamine | C₆H₁₃N | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | Cyclohexyl-(3-methyl-pyridin-2-yl)-amine | C₁₂H₁₈N₂ | 61.83% |
Conditions
- Temperature
- 115 °C
Yield
- 62% of Cyclohexyl-(3-methyl-pyridin-2-yl)-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
Ref: EN07957-77 BIS(DIBENZYLIDENEACETONE)PALLADIUM(Pd2((dba)3) (0.101 g, 0.11 mmol) and 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene (BINAP) (0.136 g, 0.22 mmol) was was stirred in toluene (16.5 mL) under N2. Then 2-bromo-3-methylpyridine (1.619 mL, 14.53 mmol), cyclohexanamine (1.662 mL, 14.53 mmol) and sodium 2-methylpropan-2-olate (2.430 g, 25.29 mmol) was added to the above reaction mixture under N2.The reaction mixture was degasssed by reapeated 3 times with N2 and vaccum before the reaction mixture was heated at 115 °C for 1.5h LCMS indicated no SM left. The reaction mixture was cooled to rt, and then diluted with EtOAc and H2O. and neutralized by citric acid to PH ca 5. The aqoeus phase was extracted with EtOAc (4 x). The combined organic layers were dried over Na2SO4 and co
The source
This record comes from experimental reaction archive (ord-273601a9c88f40afa5574d06d820673e). Open the source and check it against what is on this page.
experimental reaction archive record ord-273601a9c88f40afa5574d06d820673e 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.
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Where to next
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