Water → 3-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide

Participants

Reaction Conditions

Reaction Steps

5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (150 mg, 0:4 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbaldehyde (115 mg, 0.48 mmol, 1.2 eq), PdCl2(dppf)-CH2Cl2 adduct (29 mg, 0.04 mmol, 0.09 eq), and potassium carbonate (170 mg, 1.2 mmol, 3 eq) were diluted in dioxane (3 mL) and water (1.5 mL) in a 2-5 mL microwave tube. The mixture was degassed by bubbling argon through for 5 minutes, then the reaction was heated in a microwave oven under regular absorption at 10° C. for 5 minutes. The reaction mixture was filtered through a thiol SPE cartridge, washing well with acetone, and the solvent was removed in vacuo. The crude residue was triturated from diethyl ether to give a pink solid. Minor impurities were present, but this material was suitable for use in the reductive amination step as is (210 mg, 0.52 mmol, 129%).

Provenance & Evidence