Ethanol → 3-(5-(Tert-butylcarbamoyl)-4-formylthiophen-2-yl)-4-methylbenzoic acid

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Reaction Steps

A mixture of N-tert-butyl-5-chloro-3-formylthiophene-2-carboxamide (2.40 g, 9.77 mmol), 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (3.07 g, 11.7 mmol), Pd(PPh3)2Cl2 (0.343 g, 0.488 mmol, Strem), and sodium carbonate (3.11 g, 29.3 mmol) in DME:EtOH:H2O=7:2:3 (36 ml) was heated to 80° C. for 8 hrs. After cooling to RT, the mixture was diluted with sat. aq. NH4Cl and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered and concentrated over SiO2. Column chromatography (MeOH/CH2Cl2=0→2%) gave the desired product. Yield: 2.31 g.

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