Cesium fluoride → 2-Methyl-6-(1-methylpyrazol-4-yl)isoquinolin-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-2-methylisoquinolin-1-one (3.8 g, 16 mmol), 1-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (6.69 g, 32 mmol), CsF (7.29 g, 48 mmol), Pd(PPh3)2Cl2 (0.4 g, 1 mmol) in dioxane/H2O (60/10 mL) was stirred at 90° C. for 12 h under N2. The mixture was concentrated and the residue was purified by silica gel chromatography (PE:EA=2:1) to give the title compound (3.1 g, 81%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.40 (d, J=12 Hz, 1H), 7.87 (s, 1H), 7.74 (s, 1H), 7.59-7.56 (dt, J1=4 Hz, J2=8 Hz, 2H), 7.07 (d, J=4 Hz, 1H), 6.48 (d, J=8 Hz, 1H) 3.98 (s, 3H), 3.61 (s, 3H). LCMS: 240.0 (M+H)+

Provenance & Evidence