Triethylamine → HCID 89812812, compound

Participants

Reaction Steps

4-[4-(5-Bromo-1-oxo-1,2-dihydro-isoquinolin-3-yl)benzyl]piperazine-1-carboxylic acid (140.0 mg, 0.281 mmol), ethynyltrimethylsilane (119 μL, 0.843 mmol), triethylamine (391 μL, 2.81 mmol), dichlorobis(triphenylphosphine)palladium(II) (19.6 mg, 0.028 mmol), and triphenylphosphine (3.67 mg, 0.014 mmol) in anhydrous DMF (3 mL) were added to a microwave vial and the reaction mixture purged with N2 for 5 min. Copper (I) iodide (5.33 mg, 0.028 mmol) was added and the mixture was degassed for a further minute. The reaction mixture was irradiated using a microwave reactor (300 W, 110° C., 1 h). The reaction mixture was then concentrated in vacuo, diluted with water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic layer was washed with brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography, eluting with iso-hexane and increasing the polarity to 100% EtOAc/iso-hexane to afford 4-[4-(1-oxo-5-trimethylsilanylethynyl-1,2-dihydroisoquinolin-3-yl)benzyl]piperazine-1-carboxylic acid tert-butyl ester as a yellow solid (70.3 mg, 49%).

Provenance & Evidence