Buchwald–Hartwig amination: 3-(2-chloro-5-fluoro-4-pyridinyl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]azepine → tert-butyl N-[(1R,3S)-3-[[5-fluoro-4-(5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]azepin-3-yl)-2-pyridinyl]carbamoyl]cyclohexyl]carbamate

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

120 °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.

• tert-butyl N-[(1R,3S)-3-[[4-(6,6-dimethyl-5,7-dihydropyrrolo[1,2-a]imidazol-3-yl)-5-fluoro-2-pyridinyl]carbamoyl]cyclohexyl]carbamate80%
• tert-butyl N-[(1R,3S)-3-[[4-(5,5-dimethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyridin-3-yl)-5-fluoro-2-pyridinyl]carbamoyl]cyclohexyl]carbamate53%
• tert-butyl N-[(1R,3S)-3-[[5-fluoro-4-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)-2-pyridinyl]carbamoyl]cyclohexyl]carbamate37%
• tert-butyl N-[(1R,3S)-3-[[4-(5,5-dimethyl-4,6-dihydropyrrolo[2,1-e]pyrazol-3-yl)-5-fluoro-2-pyridinyl]carbamoyl]cyclohexyl]carbamate35%

Copied from the source record, unedited

Tetrakis(triphenylphosphine)palladium(0) (0.304 g, 0.26 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]azepine (0.700 g, 2.63 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (0.638 g, 2.63 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.305 g, 0.53 mmol) and Cesium carbonate (2.58 g, 7.90 mmol) in 1,4-dioxane (10 mL)Degassed for 5 mins under nitrogen and the resulting suspension was stirred at 120 °C for 17 hours in the microwave reactor. The reaction mixture was partitioned between water (20ml) and ethyl acetate (100ml) filtered and separated. The organics were absorbed onto silica and purified by flash silica chromatography, elution gradient 1:1 EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-bu

This record comes from experimental reaction archive (ord-5545e57a105549059abb855326d6ce2b). Open the source and check it against what is on this page.

• experimental reaction archive record ord-5545e57a105549059abb855326d6ce2b 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.