Buchwald–Hartwig amination: 6-chloro-N-cyclohexylpyridine-3-carboxamide → 6-(4-cyanoanilino)-N-cyclohexylpyridine-3-carboxamide

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

100 °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.

Copied from the source record, unedited

In a 50 mL round-bottomed flask a TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.115 g, 0.13 mmol),POTASSIUM TERT-BUTOXIDE (0.282 g, 2.51 mmol)and BINAP (0.157 g, 0.25 mmol) in dry 1,4-dioxane (10 mL) was mixed under N2.Followed by 6-chloro-N-cyclohexylnicotinamide (.300 g, 1.26 mmol) and 4-aminobenzonitrile (0.178 g, 1.51 mmol) was added and resulting mixture(dark brown) was heated at 100oC for 3 hrs.LCMS analysis showed the formation of required product.Reaction stopped,crude was passed through celite and washed with dioxane and finally with methanol.The filtrate was dried and dissolved in 3 ml DMSO for Waters MS Purification system.Pure fractions collected and concentrated.A White solid obtained as a product 6-(4-cyanophenylamino)-N-cyclohexylnicotinamide (0.040 g, 9.93 %).32 mg of above p

This record comes from experimental reaction archive (ord-2d4104aef43247ff855d465ce3910528). Open the source and check it against what is on this page.

• experimental reaction archive record ord-2d4104aef43247ff855d465ce3910528 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

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experimental reaction record.