Buchwald–Hartwig amination: 3,5-Dibromopyridine → 4-(5-Bromopyridin-3-yl)morpholine

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%
• 5-bromo-N-(2-methoxyethyl)-N-methylpyridin-3-amine68%
• N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-3,3-dimethyl-butyramide64%
• 4-(6-Bromopyridin-3-yl)morpholine56%
• 3-bromo-5-[(3R)-3-methoxypyrrolidin-1-yl]pyridine51%
• Methyl 3-bromo-4-morpholinobenzoate32%
• 1-[4-(5-Bromo-3-pyridinyl)piperazin-1-yl]ethanone32%
• 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%
• 1-(5-Bromopyridin-3-yl)-4-methylpiperazine21%

Copied from the source record, unedited

A mixture of 3,5-dibromopyridine (3.01 mL, 12.66 mmol), morpholine (1.00 g, 11.48 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM (0.210 g, 0.23 mmol), sodium 2-methylpropan-2-olate (1.655 g, 17.22 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.429 g, 0.69 mmol) in degassed toluene (35 mL) was stirred for 16 hours at 110 °C in a sealed vessel under inert atmosphere. Extraction with sat. aq. Na2CO3 solution and AE, then back extraction 2x NaCl sat using DCM. The organics were dried over MgSO4 and evaporated _in vacuo_. The residue (see structure below, LC MS FLA-04227-45-02: 3,5 dimorpholino pyridine) was washed off with diethylether, then AE. The liquors were vaporated _in vacuo_. The residue was purified by chromatography (11 cm SiO2, diameter: 5 cm) eluent: AE/hex 25/75to 45/55 to

This record comes from experimental reaction archive (ord-822f9545d2954337a3563b98247b8f3b). Open the source and check it against what is on this page.

• experimental reaction archive record ord-822f9545d2954337a3563b98247b8f3b 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.