Water → HCID 59332669, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (3-formylphenyl)boronic acid (0.121 g, 0.808 mmol), 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (0.150 g, 0.404 mmol) and Potassium carbonate (0.168 g, 1.212 mmol) in 1,4-Dioxane (1.796 mL)/Water (0.898 mL) was degassed with nitrogen for several minutes and PdCl2(dppf) (0.030 g, 0.040 mmol) was added. The mixture was heated at 100° C. for 5 minutes in the microwave on ‘high’ absorption setting. The aqueous layer was removed via pipette and the reaction mixture was filtered through a 500 mg Stratospheres PL Thiol SPE cartridge, eluting with 10 mL of DCM/MeOH (1:1). Crude LCMS shows the desired compound as major peak. Concentrated under nitrogen to obtain 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(3-formylphenyl)-1H-indole-7-carboxamide (0.160 g, 0.404 mmol, 100% yield).

Provenance & Evidence