2-Bromopropane → 2-(3,5-Dichloro-2-isopropoxy-benzenesulfonylamino)-indan-2-carboxylic acid ethyl ester

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Reaction Steps

To a suspension of 2-(3,5-dichloro-2-hydroxy-benzenesulfonylamino)-indan-2-carboxylic acid ethyl ester (30) (226 mg, 0.53 mmol), anhydrous Cs2CO3 (300 mg, 0.92 mmol), and KI (15 mg, 0.09 mmol) in DMF (15 mL) is added 2-bromopropane (432, 4.60 mmol). The resulting reaction suspension is filled with argon and run in a microwave reaction: 110° C., 2.5 h. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (30 mL) and washed with water (1×5 mL) and brine (2×5 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%-60% EtOAc in heptane) to give a pure product (31) as a white semi-solid (248 mg, 100%).

Provenance & Evidence