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

Participants

Reaction Conditions

Reaction Steps

In a 5 mL microwave vial was added 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxamide (55 mg, 0.131 mmol), PdCl2(dppf)-CH2Cl2 adduct (17.18 mg, 0.021 mmol), and K2CO3 (83 mg, 0.601 mmol). Then 3-(4-bromo-2-thienyl)-1-propanol (37.8 mg, 0.171 mmol) in 1,4-dioxane (3 mL) was added to give an orange solution. Water (1.5 mL) was added and the solution was heated to 100° C. at high power in the microwave for 5 min, cooled. The reaction was filtered through a thiol paladium extraction column. The column was washed with CH2Cl2 and the combined filtrates were concentrated and purified on a Gilson HPLC(NH4OH buffer), giving 23 mg (41%) of the title compound.

Provenance & Evidence