3-Chlorosalicylic acid → 2-(3-Chloro-2-hydroxy-benzoylamino)-indan-2-carboxylic acid ethyl ester

Participants

Reaction Steps

To a solution of 3-chloro-2-hydroxy-benzoic acid (413 mg, 2.4 mmol), 2-Amino-indan-2-carboxylic acid ethyl ester (500 mg, 2.4 mmol), HATU (1.1 g, 2.9 mmol) in anhydrous DMF (10 mL) is added DIPEA (0.88 ml, 5.3 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (50 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (120 g silica gel, gradient elution: 10%-80% EtOAc in heptane) to give a pure product (14) as white solid (420 mg, 49%).

Provenance & Evidence