Potassium Carbonate → HCID 59415759, compound

Participants

Reaction Conditions

Reaction Steps

(1S,2S)-(+)-1,2-Diaminocyclohexane (500 mg, 4.3 mmol) was added to the solution of (Z)-ethyl-3-(dimethylamino)-2-(3-iodobenzoyl)acrylate (Intermediate 24, 0.34M, 11.7 mL, 3.9 mmol) and the mixture was heated at 50° C. for 3 h. The solvent was removed in vacuo and the residue was dried in a vacuum oven for 1.5 h. The residue was then dissolved in dimethyl formamide (7 mL) and potassium carbonate powder (753 mg, 5.5 mmol) was added. The reaction was heated at 70° C. for 3 h then cooled to room temperature. Water (30 mL) was added and the suspension was extracted with 1:1 ethyl acetate:methyl tert-butyl ether (3×50 mL). The organic layers were dried over sodium sulfate, and the solvent was removed in vacuo. The residue was suspended in methyl tert-butyl ether (20 mL) and stirred at 40° C. for 1 h. The suspension was filtered and the solid dried to give 724 mg (42% yield) of ethyl 1-((1S ,2S)-2-aminocyclohexyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate as a yellowish powder that was contaminated with about 40% bis dihydroquinoline. This material was used as is in the coupling step.

Provenance & Evidence