tert-butyl N-[(E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-enyl]carbamate

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]carbamate (3-3) (32.5 mg, 0.115 mmol, 4 eq) and 6-bromobenzo[g][1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (7-6) (9.0 mg, 0.029 mmol, 1 eq) in THF (0.5 ml) was added a solution of cesium carbonate (18.7 mg, 0.058 mmol, 2 eq) in water (0.2 ml), and the resulting mixture was deoxygenated with nitrogen and treated with Pd(dppf) (1.0 mg, 0.0014 mmol, 0.05 eq). The reaction mixture was deoxygenated again, and heated in a sealed tube under microwave irradiation for 8 min at 150° C. The resulting suspension was filtered through a pad of Celite washing with DMF, and the filtrate was purified on RP HPLC (MeCN/Water with TFA) to afford the desired coupling product 7-7. LRMS m/z: found 391.2, calcd. (M+H) 391.2. the resulting mixture was deoxygenated with nitrogen The reaction mixture was deoxygenated again The resulting suspension was filtered through a pad of Celite washing with DMF the filtrate was purified on RP HPLC (MeCN/Water with TFA)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-bromo-9-chloro[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (3-9) (60 mg, 0.201 mmol, 1.0 equiv.) and tert-butyl[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]carbamate (3-3) (228 mg, 0.804 mmol, 4.0 equiv.) were dissolved in anhydrous 1,4-dioxane (0.6 ml) and 2 M K2CO3 aqueous solution (0.2 mL). The reaction mixture was heated to 100° C. LCMS at 18 hours showed complete conversion. Purification with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA) afforded the title product 3-10. LRMS m/z (M+H) 375.1 found, 375.1 required. Purification with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA)