Potassium Carbonate → 5-(5-formyl-3-thienyl)-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

To 5-bromo-3-(1-{[3-(methyloxy)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (170 mg, 0.37 mmol) in mixture of dioxane (4.5 mL) and water (1.5 mL), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbaldehyde (265.2 mg, 1.11 mmol), potassium carbonate (309 mg, 2.22 mmol) and Pd(PPh3)4 (44.2 mg, 0.04 mmol) were added. The reaction mixture was heated by microwave at 150° C. for 20 minutes. Then all the solvent was evaporated. The residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The water layer was extracted with ethyl acetate (2×50 mL). The combined organic phase washed with brine (50 mL) and dried with Mg2SO4 and concentrated. The crude product was purified by Combiflash (dichloromethane/methanol, 1%-40% methanol, 25 min.) to give title compound (110 mg, 61%).

Provenance & Evidence