1-Pyrrolidineethanamine → HCID 24771537, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried pyrex screw-tube was charged with rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ((rac)-BINAP) (0.3 equiv., 0.138 mmol, 0.086 g), Pd2(dibenzylidene-acetone)3 (Pd2 dba3) (0.1 equiv., 0.046 mmol, 0.042 g) and Cs2CO3 (1.4 equiv., 0.643 mmol, 0.210 g). Dry dioxane (1 ml) was added and the screw-tube was purged with Ar. The reaction mixture was heated at 80° C. for 30 min, after which it was allowed to cool to room temperature. 9-Bromo-6-(4-nitrophenyl)-pyrido[2′,1′:2,3]-imidazo[4,5-c]isoquinolin-5(6H)-one (18) (1.0 equiv., 0.460 mmol, 0.200 g) and pyrrolidineethanamine (1.0 equiv., 0.460 mmol, 0.052 g) were added and the reaction mixture was stirred at 100° C. until no starting materials were left. The progress of the reaction was monitored by LCMS. Removal of the solvent under reduced pressure, followed by column chromatography (gradient elution: dichloromethane→dichloromethane/methanol 9:1) of the resulting residue gave 6-(4-nitrophenyl)-9-(2-pyrrolidin-1-yl-ethylamino)-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one (67) (0.055 g, yield=26%, purity (LC)=97%).

Provenance & Evidence