Buchwald–Hartwig amination: 2,4-Dichloropyridine → Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate
0% yield, run at 160 °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 | 2,4-Dichloropyridine | C₅H₃Cl₂N | |
| Reactant | Ethyl 2-amino-1,3-oxazole-5-carboxylate | C₆H₈N₂O₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Bis(3,5-bis(trifluoromethyl)phenyl)(3,6-dimethoxy-2',4',6'-tri(propan-2-yl)(1,1'-biphenyl)-2-yl)phosphane | C₃₉H₃₇F₁₂O₂P | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate | C₁₁H₁₀ClN₃O₃ | 0% |
Conditions
- Temperature
- 160 °C
Yield
- 0% of Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate.
Procedure
Copied from the source record, unedited
Objective: Attempt to synthesise the 4-substituted product using jackiephos as ligand. To an oven-dried microwave vial was added ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol), 2,4-dichloropyridine (0.108 mL, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol) and bis(3,5-bis(trifluoromethyl)phenyl)(2',4',6'-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (80 mg, 0.10 mmol) and the vial was capped and purged with nitrogen. dioxane (4 mL) (degassed) was added and the reaction mixture was heated to 160 °C for 1 h under microwave irradiation. The reaction mixture was heated to 160°C for a further 3 h due to incomplete conversion. DCM (10 mL) was added to the crude reaction mixture together with silica (2 g). The solvent
The source
This record comes from experimental reaction archive (ord-0e2b144c96fd4ac8aced468951db5ce4). Open the source and check it against what is on this page.
experimental reaction archive record ord-0e2b144c96fd4ac8aced468951db5ce4 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
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