Triethylamine → 3-Chloro-5-[(1H-indazol-4-ylmethyl)-carbamoyl]-thiophene-2-carboxylic acid methyl ester

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Reaction Steps

To a solution of 3-Chloro-thiophene-2,5-dicarboxylic acid 2-methyl ester (200 mg, 0.91 mmol) in anhydrous DMF (5 mL) was added triethylamine (0.38 mL, 2.73 mmol), HBTU (0.52 g, 1.37 mmol), HOBT (0.147 mg, 1.09 mmol), and C-(1H-Indazol-4-yl)-methylamine (146 mg, 1.0 mmol). The mixture was stirred at room temperature 15 h, then quenched by pouring into EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 0-70% EtOAc in hexane to afford the desired product (0.073 g, 23% yield).

Provenance & Evidence