Potassium Carbonate → 5-(2-chloro-4-pyridinyl)-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of (2-chloro-4-pyridinyl)boronic acid (0.095 g, 0.606 mmol), 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (0.075 g, 0.202 mmol) and potassium carbonate (0.168 g, 1.212 mmol) was added 1,4-dioxane (0.898 mL)/water (0.449 mL). The mixture was degassed with nitrogen and PdCl2(dppf) (0.015 g, 0.020 mmol) was added. The reaction mixture was heated in a microwave oven at 100° C. for 5 minutes on ‘high’ absorption setting. LCMS of crude reaction mixture shows the desired m/z and some unreacted starting material (very close ret. times). The reaction mixture was filtered through a Thiol SPE cartridge (500 mg) eluting with 1:1 MeOH/DCM (10 mL). The filtrate was purified with RP-HPLC (XBridge Column, 0.1% NH4OH). The fractions containing the desired compound are combined and concentrated to give 5-(2-chloro-4-pyridinyl)-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (0.016 g, 19.61%).

Provenance & Evidence