Sodium Chloride → (rac)-6-(7-Amino-6,7-dihydro-5H-cyclopenta[c]pyridin-4-yl)-1-methyl-3,4-dihydroquinolin-2(1H)-one

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Reaction Conditions

Reaction Steps

In a 50 ml round-bottomed flask, (rac)-4-bromo-6,7-dihydro-5H-cyclopenta[c]pyridin-7-amine (intermediate A-3[C]) (107 mg, 500 μmol) and 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one (intermediate A-1) (172 mg, 600 μmol) were dissolved in EtOH (9 mL) to give a brown solution. Na2CO3 (58.3 mg, 550 μmol), dissolved in water (1.5 mL) was added followed by tetrakis(triphenylphosphine)palladium (0) (17.3 mg, 15.0 mmol) after evacuation and replacing 5 times with Argon. The suspension was then heated at 85° C. overnight. A aq. 10% NaCl solution was added at RT, and the mixture was extracted with AcOEt (3×). The organic fractions were washed again with aq. 10% NaCl solution, dried over Na2SO4, filtered, evaporated and purified by flash chromatography (50 g SiO2, Telos-cartridge, CH2Cl2/MeOH (2%)) to afford the title compound (21 mg, 14%) as a dark green powder. MS: 294.2 (M+H+)

Provenance & Evidence