Sodium Carbonate → tert-Butyl 6-[2-(trifluoromethyl)pyrimidin-5-yl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 4:1 mixture (0.10 g, 0.28 mmol) of tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate and tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate, 2-(trifluoromethyl)pyrimidin-5-yl trifluoromethanesulfonate (0.083 g, 0.28 mmol), PdCl2×dppf (0.0048 g), 2M sodium carbonate (1.1 mL), toluene (4.0 mL) and EtOH (1.0 mL) was purged with dry argon for ten minutes then heated in a sealed vial at 81° C. for 6 h. The black solution was filtered through glass-wool, taken up in water-brine and washed twice with EtOAc. The combined organic phases were dried, filtered and concentrated with silica (5 g). Column chromatography with EtOAc-heptanes (1:8 through 1:5) gave 0.051 g (48%) of the title product as white solid.

Provenance & Evidence