Dimethylformamide → HCID 59314118, compound

Participants

Reaction Steps

A 30 mL reaction vial is charged with 2-(2-hydroxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (3, 400 mg, 1.18 mmol) and dry DMF (5 mL). A stirring bar is added and stirring is initiated. After dissolution, K2SO4 (326 mg, 2.36 mmol) and bromoacetonitrile (164 μL, 2.36 mmol) are added in turn. The reaction vial is capped and placed in a heating block which is set atop of an orbital shaker. The heating block is set at 55° C. After 16 h, tlc analysis (silica, 1:1 EtOAc in heptanes) indicates that the starting material is completely consumed. Heating is terminated. After sitting at ambient temperature for 1 day, the contents of the flask are filtered through a pad of Celite. The filtrate is transferred to a reparatory funnel which contains EtOAc (40 mL). The layers are separated. The organic phase is washed with water (20 mL), saturated aqueous NaHCO3 and brine (20 mL), and then dried over MgSO4, filtered and concentrated by pumping to constant weight to give dark brown solid (0.42 g). This material is dissolved in 10 mL of DCM. This material is purified utilizing an ISCO Companion with a 25 g cartridge of silica. The gradient is 10% EtOAc in heptanes over 3 column volumes followed by a linear gradient to 50% EtOAc in heptanes over 10 column volumes. 17 mL fractions of eluent are collected. Fractions 4 through 6 are combined and evaporated in vacuo. This provides white solid (0.26 g, 58%).

Provenance & Evidence