3-Methylsalicylic Acid → 2-(2-Hydroxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

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Reaction Steps

To a solution of 2-hydroxy-3-methyl-benzoic acid (3.65 g, 24 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (5.00 g, 24 mmol), HATU [O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium PF6] (11.0 g, 29 mmol) in anhydrous DMF (30 mL) is added DIPEA (8.30 mL, 50 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (150 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 (400 g silica gel, gradient elution: 10-80% EtOAc in heptane) to give a pure product (3) as white solid (5.5 g, 67%).

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