Buchwald–Hartwig amination: 2-Chloro-6-(trifluoromethyl)pyridine → Ethyl 2-[[6-(trifluoromethyl)-2-pyridinyl]amino]-1,3-oxazole-5-carboxylate

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

Temperature

160 °C

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

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-[(5-nitro-2-pyridinyl)amino]-1,3-oxazole-5-carboxylate86%
• 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%

Copied from the source record, unedited

Objective: To test substrate scope in 5-ester substituted 2-aminooxazole coupling. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (22.87 mg, 0.02 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (43.4 mg, 0.075 mmol), cesium carbonate (651 mg, 2.00 mmol), ethyl 2-aminooxazole-5-carboxylate (156 mg, 1.00 mmol) and 2-chloro-6-(trifluoromethyl)pyridine (181 mg, 1.00 mmol) were placed in an oven dried microwave vial. The vial was then capped and placed under an inert atmosphere. Dioxane (4 mL) was added and the mixture was heated to 160 °C for 1 h under microwave irradiation. LCMS of the crude reaction mixture indicated the presence of the desired product. DCM (10 mL) was added to the crude reaction mixture together with C-18 silica (2 g), and the solvent was removed under reduced

This record comes from experimental reaction archive (ord-006fb353766e418abd7ffca7f96dda71). Open the source and check it against what is on this page.

• experimental reaction archive record ord-006fb353766e418abd7ffca7f96dda71 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

  experimental record · quality medium · source

experimental reaction record.