Buchwald–Hartwig amination: Morpholine → Ethyl 4-(2-fluoro-4-methylanilino)-7-(2-methoxyethoxy)-6-morpholin-4-ylquinoline-3-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

80 °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.

• Dimethyl 5-morpholinoisophthalate78%
• N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-3,3-dimethyl-butyramide64%
• 4-(6-Bromopyridin-3-yl)morpholine56%
• 4-(5-Bromopyridin-3-yl)morpholine50%
• Methyl 3-bromo-4-morpholinobenzoate32%
• 4-Morpholinophenol31%
• 2,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(4-morpholin-4-ylphenyl)methyl]benzamide30%
• 5-Morpholin-4-yl-nicotinic acid tert-butyl ester27%
• (5-Morpholinopyridin-2-yl)methanol19%
• 2,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(3-morpholin-4-ylphenyl)methyl]benzamide18%
• Methyl 5-bromo-2-morpholinobenzoate18%
• 2-Cyclopentyl-N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-acetamide13%

Copied from the source record, unedited

Reaction reference EN00057-06, EN02095-49, 67, 68, 74, 78, 90 In a 50 mL round-bottomed flask was ethyl 6-bromo-4-(2-fluoro-4-methylphenylamino)-7-(2-methoxyethoxy)quinoline-3-carboxylate (4.6911 g, 9.83 mmol), Morpholine (0.857 mL, 9.83 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.720 g, 0.79 mmol), and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (1.958 g, 3.14 mmol) in Dioxane (100 mL) to give a orange suspension. The reaction mixture was heated and stirred at 80°C (start 4pm). After stirring/heating overngiht, reaction is about 30% complete. Add rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (1.958 g, 3.14 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.720 g, 0.79 mmol). Continue heating/stirring. After heating and stirring for another 24hr, reaction is about 85% com

This record comes from experimental reaction archive (ord-b3b59923db4e4673a6bcde3d5a9c7727). Open the source and check it against what is on this page.

• experimental reaction archive record ord-b3b59923db4e4673a6bcde3d5a9c7727 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.