Buchwald–Hartwig amination: N-[(4-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)-(4-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

130 °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%
• 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

In a CEM microwave vial was N-((4-bromophenyl)(7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)methyl)-2,6-dimethylbenzamide (100 mg, 0.23 mmol), morpholine (0.082 mL, 0.94 mmol), palladium(II) acetate (5.25 mg, 0.02 mmol), BINAP (14.57 mg, 0.02 mmol), and potassium tert-butoxide (52.5 mg, 0.47 mmol) solid and DMF (2 mL) was added. The vial was capped and placed into the microwave at 300 watts, 130 °C for 4 minutes. After reaction completion, the the mixture was concentrated and crude taken up in CH2Cl2 and washed with water and dried (Na2SO4). The material was purified on a 12 gram Isco silica cartridge and eluted with 0% to 5% MeOH 2M NH3/CH2Cl2 to give a light yellowish solid 2,6-dimethyl-N-((7-methyl-7-azabicyclo[2.2.1]heptan-1-yl)(4-morpholinophenyl)methyl)benzamide (30.0 mg, 29.6 %).

This record comes from experimental reaction archive (ord-ea53d8feb8094f94b89810756f770f19). Open the source and check it against what is on this page.

• experimental reaction archive record ord-ea53d8feb8094f94b89810756f770f19 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.