1,2-Dimethoxyethane → HCID 68524427, compound

Participants

Reaction Conditions

Reaction Steps

Add DME (3 mL) to a mixture of 3-[4-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-[1,2,4]thiadiazole (0.066 g, 0.23 mmol), 4-Cyano-3-iodo-5-ethyl-thiophene-2-carboxylic acid ethyl ester (0.071 g, 0.20 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride (1:1) dichloromethane complex (0.009 g, 0.01 mmol) and cesium fluoride (0.103 g, 0.68 mmol) under nitrogen and stir at 80° C. for 3 h. Cool down and add ice-water and ethyl acetate. Separate layers and wash the organic layer with water (3×) and back-extract the combined aqueous layers with ethyl acetate (2×). Wash the combined organic layers with brine, dry over anhydrous sodium sulfate and concentrate under reduced pressure over Celite®. Purify by flash chromatography (silica gel) eluting with hexanes-ethyl acetate 10:1 first, then 5:1 to give 0.06 g of the title compound as a white solid. Mass spectrum ESI positive (m/z): 370 (M+1).

Provenance & Evidence