Buchwald–Hartwig amination: 3-(2-Chloro-5-methylpyrimidin-4-yl)pyrazolo[1,5-a]pyridine → 1-[5-Methoxy-6-[(5-methyl-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)amino]-2,3-dihydroindol-1-yl]ethanone

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

90 °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

A mixture of 3-(2-chloro-5-methylpyrimidin-4-yl)pyrazolo[1,5-a]pyridine (400 mg, 1.55 mmol), 1-(6-amino-5-methoxyindolin-1-yl)ethanone (341 mg, 1.55 mmol) and diacetoxypalladium (34.9 mg, 0.16 mmol) 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (97 mg, 0.16 mmol) cesium carbonate (759 mg, 2.33 mmol) were degassed with nitrogen then dioxane (7 mL) was added to mixture and the solution was degassed under vacuum and placed under nitrogen. The resulting suspension was stirred at 90 °C for 5hours. Control uplc/ms OK Control t.l.c : 100%EtOAc and 5%MeOH/CH2Cl2 After cooling, the mixture was filtered and the filtrate evaporated to dryness after addition of silica gel The crude product was purified by flash chromatography on silica gel 45g Merck column solid injectioneluting with 0 to 10%MeOH/Et

This record comes from experimental reaction archive (ord-019ad9f92b5c40ecbf5416e8a6461063). Open the source and check it against what is on this page.

• experimental reaction archive record ord-019ad9f92b5c40ecbf5416e8a6461063 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.