Dichloromethane → HCID 59314165, compound

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Reaction Steps

A 100 mL round bottom flask is charged with 2-aminoindan-2-carboxylic acid (340 mg, 1.66 mmol) and dry DCM (6 mL). A stirring bar is added and stirring is initiated. DIPEA (0.46 mL, 2.65 mmol) is added. 2-[(2,2-difluoro-benzo[1,3]dioxole-4-carbonyl chloride (438 mg, 1.99 mmol) is added. 4-Dimethylaminopyridine ([MFCD0006418], 2 mg, cat.) is added. The reaction is capped. After 18 days, tlc analysis (silica, 5% iPrOH/DCM) indicates that the starting is completely consumed. The contents of the reaction flask are transferred to a reparatory funnel and diluted with EtOAc (60 mL). This is washed with dilute aqueous HCl (2×25 mL), saturated aqueous NaHCO3 (2×25 mL), and brine (25 mL), dried over MgSO4, filtered and evaporated by pumping to constant weight to yield 0.73 g of dark brown foam. This is diluted with DCM and applied to a silica column (40 g) on an ISCO Companion. The column is eluted with 3 column volumes of 10% EtOAc-heptanes followed by a linear gradient to 50% EtOAc/heptanes over 10 Column Volumes. And then 90% EtOAc/heptanes for 2 Column Volumes. 17 mL fractions of UV positive eluent are collected. Fraction 8-10 are combined and evaporated by pumping to constant weight to give light orange solid (0.57 g, 88%).

Provenance & Evidence