1-Methylpiperazine → Ethyl 4-[(2,4-dichlorophenyl)amino]-7-methoxy-6-(4-methylpiperazin-1-yl)quinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

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, repeat.

Provenance & Evidence