Ethylenediamine → HCID 68828573, compound

Participants

Reaction Conditions

Reaction Steps

Palladium acetate (0.030 g, 0.13 mmol) and racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.25 g, 0.40 mmol) were added to toluene (20 ml) under a nitrogen atmosphere and the mixture was stirred at 40° C. for 30 min. The reaction mixture was cooled to room temperature and 6-bromo-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (1.0 g, 2.6 mmol), ethylenediamine (0.44 ml, 6.6 mmol) and sodium tert-butoxide (0.35 g, 3.7 mmol) were added. The mixture was stirred under a nitrogen atmosphere at 80° C. for 2 hrs. The reaction mixture was cooled and partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate. The aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, and the mixture was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in tetrahydrofuran (100 ml). Di-tert-butyl dicarbonate (0.73 ml, 3.2 mmol) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give tert-butyl 2-{[3-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]amino}ethylcarbamate (0.85 g, yield 70%) as a pale-yellow powder.

Provenance & Evidence