Buchwald–Hartwig amination: Ethyl 6-bromo-4-[(2,4-dichlorophenyl)amino]-7-methoxyquinoline-3-carboxylate → Ethyl 4-[(2,4-dichlorophenyl)amino]-7-methoxy-6-(4-methylpiperazin-1-yl)quinoline-3-carboxylate

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

100 °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.

• N-[5-(4-methylpiperazin-1-yl)pyrazin-2-yl]acetamide80%
• Methyl 3-(4-methyl-1-piperazinyl)-5-nitrobenzoate65%
• Methyl 4-((3-(4-methylpiperazin-1-yl)pyridin-2-yl)methoxy)benzoate64%
• 1-(4-Chloro-2-methoxyphenyl)-4-methylpiperazine64%
• 4-(4-Methyl-1-piperazinyl)phenol51%
• 1-(5-Bromopyridin-3-yl)-4-methylpiperazine21%
• 1-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)-4-methylpiperazine0%
• Ethyl 4-[(2,4-difluorophenyl)amino]-6-(4-methylpiperazin-1-yl)quinoline-3-carboxylate0%
• N-[5-(1H-imidazol-2-yl)-2-methylphenyl]-4-[[3-(4-methylpiperazin-1-yl)-2-pyridinyl]methoxy]benzamide0%
• 1-(4-Chloro-2-methoxyphenyl)-4-methylpiperazine0%

Copied from the source record, unedited

To a solution of ethyl 6-bromo-4-(2,4-dichlorophenylamino)-7-methoxyquinoline-3-carboxylate (694 mg, 1.48 mmol) and 1-methylpiperazine (0.246 mL, 2.21 mmol) in dioxane (10 mL) was added cesium carbonate (962 mg, 2.95 mmol), tris(dibenzylideneacetone)dipalladium(0) (67.6 mg, 0.07 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (92 mg, 0.15 mmol). Reaction vessel in oil bath set to 100 °C. 2.15pm o/n 20 hours - LCMS shows product (489) and SM (470) 26 hours - ratio of product : SM looks better by MS. 2 x o/n - small SM peak remaining in MS. Concentrated onto silica and purified on ISCO. 40g column, 4:1 H:EA, then gradient up to ~1:1 EA:MeOH. Can't find product by LCMS in any fractions. NMR of polar fractions may be acid from Buchwald coupling. Need to purify SM on column, rep

This record comes from experimental reaction archive (ord-805e4c9d19604f5ca8a6f376906a62c5). Open the source and check it against what is on this page.

• experimental reaction archive record ord-805e4c9d19604f5ca8a6f376906a62c5 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.