Buchwald–Hartwig amination: N-(4-Bromo-2,6-dimethyl-phenyl)-3,3-dimethyl-butanamide → N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-3,3-dimethyl-butyramide

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%
• Ethyl 4-(2-fluoro-4-methylanilino)-7-(2-methoxyethoxy)-6-morpholin-4-ylquinoline-3-carboxylate75%
• 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

Exemplar cmpd from , though employing slightly different Buchwald-Hartwig coupling conditions. Tris(dibenzylidenacetone)dipalladium(0) (31 mg, 0.03 mmol) and 2'-(dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (27 mg, 0.07 mmol) were stirred in anhydrous toluene (3 mL) for 15 minutes under an argon (g) sparge. To the stirring soluntion was added the N-(4-bromo-2,6-dimethylphenyl)-3,3-dimethylbutanamide (200 mg, 0.67 mmol) and morpholine (0.070 mL, 0.80 mmol) neat, followed by the potassium tert-butoxide (1M in THF) (0.94 mL, 0.94 mmol) via syringe. The mixture was then heated in a sealed vessel to 80 °C for 18hrs before cooling to ambint temperature. The mixture was filtered thru a 0.7uM GMF. The resultant crude solution was subject to flash chromatorgraphy (SiO2 \- 12 g; gradient elu

This record comes from experimental reaction archive (ord-2683b0f554e64a9e9de3f6ed71e783e9). Open the source and check it against what is on this page.

• experimental reaction archive record ord-2683b0f554e64a9e9de3f6ed71e783e9 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.