Buchwald–Hartwig amination: 2-Chloro-5-nitropyridine → Ethyl 2-[(5-nitro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate
86% 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-Chloro-5-nitropyridine | C₅H₃ClN₂O₂ | |
| Reactant | Ethyl 2-amino-1,3-oxazole-5-carboxylate | C₆H₈N₂O₃ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | Ethyl 2-[(5-nitro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate | C₁₁H₁₀N₄O₅ | 85.62% |
Conditions
- Temperature
- 160 °C
Yield
- 86% of Ethyl 2-[(5-nitro-2-pyridinyl)amino]-1,3-oxazole-5-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.
- Ethyl 2-[[6-(trifluoromethyl)-2-pyridinyl]amino]-1,3-oxazole-5-carboxylate68%
- Ethyl 2-[(5-ethoxycarbonyl-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate67%
- Ethyl 2-[[5-(trifluoromethyl)-2-pyridinyl]amino]-1,3-oxazole-5-carboxylate61%
- Ethyl 2-[(4-cyano-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate60%
- Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate48%
- Ethyl 2-[(6-cyanopyrazin-2-yl)amino]-1,3-oxazole-5-carboxylate47%
- Ethyl 2-(pyridin-2-ylamino)-1,3-oxazole-5-carboxylate38%
- Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate0%
- Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate0%
- Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate0%
- Ethyl 2-[(4-chloro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate0%
Procedure
Copied from the source record, unedited
Objective: Test of substrate scope in couple of ester substituted aminooxazole To an oven-dried microwave vial was added ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol), cesium carbonate (651 mg, 2.00 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol) 2-chloro-5-nitropyridine (158 mg, 1.00 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.4 mg, 0.07 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. LCMS of the crude reaction mixture indicated that the desired product had been formed while only a trace of the amine starting material remained. DCM (20 mL) was added to the crude reaction mixture together with silica (2
The source
This record comes from experimental reaction archive (ord-99625d03cee6403dbb604294d8ab8a9b). Open the source and check it against what is on this page.
experimental reaction archive record ord-99625d03cee6403dbb604294d8ab8a9b 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.
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