2-Bromobutane → 2-(2-sec-Butoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Participants

Reaction Steps

To a suspension of 2-(2-hydroxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (3) (400 mg, 1.18 mmol), anhydrous Cs2CO3 (574 mg, 2.36 mmol), and KI (40 mg, 0.24 mmol) in DMF (10 mL) is added 2-bromobutane (508 μL, 4.72 mmol). The resulting reaction suspension is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (30 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: 10-40% EtOAc in heptane) to give a pure product (12) as white solid (395 mg, 85%).

Provenance & Evidence