Sodium Carbonate → 8-chloro-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-chloro-1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl trifluoromethanesulfonate (66a, 300 mg, 0.910 mmol) in DMF (5 mL) was added 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (205 mg, 0.956 mmol), PdCl2(dppf)-DCM (74.3 mg, 0.0910 mmol), and Na2CO3 (289 mg, 2.73 mmol). The reaction mixture was degassed with N2 and stirred in a sealed tube at 80° C. for 2 days. The reaction mixture was adjusted to pH 7 and purified by preparative chromatography to give 8-chloro-7-(1-methyl-1H-pyrazol-5-yl)-3,4-dihydroisoquinolin-1(2H)-one (66b, 48 mg, 20%) as an oil.

Provenance & Evidence