Buchwald–Hartwig amination: N-[(3-bromophenyl)-(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl]-2,6-dimethylbenzamide → 2,6-dimethyl-N-[(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)-(3-morpholin-4-ylphenyl)methyl]benzamide

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%
• 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%
• Methyl 5-bromo-2-morpholinobenzoate18%
• 2-Cyclopentyl-N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-acetamide13%

Copied from the source record, unedited

To a suspension of N-((3-bromophenyl)(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl)-2,6-dimethylbenzamide (0.040 g, 0.09 mmol), MORPHOLINE (8.97 µL, 0.10 mmol), BINAP (5.83 mg, 9.36 µmol), and sodium tert-butoxide (0.013 g, 0.14 mmol) in toluene (2 mL) was added palladium(II) acetate (1.051 mg, 4.68 µmol). Nitrogen was passed through the solution for 15 min prior to being heated at 80 °C overnight. Crude LC shows starting material still present. Heated to 110oC for 2 days. Reaqction no longer progressing. Reaction mixture was concentrated in vacuo. Material was diluted with ethyl acetate, filtered thru celite and concentrated in vacuo. Submitted to purification group (52 mg in 1.6 mL DMSO). Received back dried- down fractions. Diluted with DCM, combined and concentrated to afford 2,6-d

This record comes from experimental reaction archive (ord-4e29f7f8d4e94f93bbf63ba519f77a6e). Open the source and check it against what is on this page.

• experimental reaction archive record ord-4e29f7f8d4e94f93bbf63ba519f77a6e 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.