Buchwald–Hartwig amination: (5-Bromopyridin-2-yl)methanol → (5-Morpholinopyridin-2-yl)methanol

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

110 °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%
• 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 10 mL Microwave vial was (5-bromopyridin-2-yl)methanol (500 mg, 2.66 mmol), morpholine (0.233 mL, 2.66 mmol),cesium carbonate (2166 mg, 6.65 mmol), Pd2(dba)3 (60.9 mg, 0.07 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (115 mg, 0.20 mmol) in dioxane (10 mL) () to give a brown suspension. The reaction mixture was heated to 110 °C for 3h. The reaction mixture was passed over Celite and washed with ethylacetate. The Filtrate was concentrate to dryness to get as a syrupy brown liquid. Water 30ml was added and extracted with ethylacetate (20x 2)ml. THe organic layers are collected, dried over Sodium Sulphate and concentrated to get as a liquid. The crude product was added to a silica gel column and was eluted with ethylacetate 0-70% Pure Collected fractions are evap

This record comes from experimental reaction archive (ord-d5d09a4967464981aba1493aa54fbd9b). Open the source and check it against what is on this page.

• experimental reaction archive record ord-d5d09a4967464981aba1493aa54fbd9b 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.