Sodium Carbonate → HCID 66615542, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (S)-3-(1-aminoethyl)-8-chloro-2-cyclopropylisoquinolin-1(2H)-one II-6 (878 mg, 3.35 mmol, 1.0 eq) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (815 mg, 3.92 mmol, 1.2 eq) in anhydrous DMA (10 mL) in a sealed tube, PdCl2(dppf) (219 mg, 0.27 mmol, 0.08 eq) and aqueous Na2CO3 solution (1 M, 10.0 mL, 10.0 mmol, 3.0 eq) were added and the resulting mixture was stirred at 120° C. for 3 h. The reaction mixture was allowed to cool to RT, quenched with water, and then extracted with ethyl acetate (200 mL×3). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by ISCO (silica gel cartridge, 0-8% MeOH-DCM) to afford the product, (S)-3-(1-aminoethyl)-2-cyclopropyl-8-(1-methyl-1H-pyrazol-4-yl)isoquinolin-1(2H)-one II-12 as a pink/magenta solid. ESI-MS m/z: 309.2 [M+H]+.

Provenance & Evidence