Potassium Carbonate → 3-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-[5-({methyl[2-(methyloxy)ethyl]amino}methyl)-3-thienyl]-1H-indole-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

To 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (100 mg, 0.27 mmol) in dioxane and water (3 mL/1 mL) were added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbaldehyde (116 mg), Pd(PPH3)4 (30 mg) and K2CO3 (112 mg). The reaction mixture was heated to 150° C. for 900 seconds in microwave. The organic phase was separated, concentrated, and redissolved in DMSO (3 mL). The resulting solution was split to two. NaBH3CN (30 mg), ZnCl2 (30 mg) and N-methyl-2-(methyloxy)ethanamine (50 mg) were added. The mixture was heated to 100° C. for 30 minutes in microwave which was then purified by HPLC with TFA to afford the title compound (9 mg).

Provenance & Evidence