Diisopropylethylamine → HCID 59314190, compound

Participants

Reaction Steps

A 40 mL reaction vial which contains a stirring bar is charged with 3-Fluoropyridine-2-carboxylic acid (997 mg, 7.07 mmol) and dry DCM (15 mL). Stirring is initiated. After 2 min, the HTBU (2.7 g, 7.07 mmol) is added. After 5 min, 2-Amino-indan-2-carboxylic acid ethyl ester (1.45 g, 7.07 mmol) is added followed by DIPEA (2.50 mL, 14.5 mmol). The reaction is allowed to stir for 18 h. Analysis by tlc of the reaction mixture (silica, 5% iPrOH/DCM) indicates complete consumption of the starting amine. The contents of the reaction flask are transferred to a separatory funnel and diluted with EtOAc (50 mL). This is washed consecutively with water (3%, 25 mL), saturated aqueous NaHCO3 (2×25 mL) and brine (25 mL), and then dried over MgSO4, filtered and evaporated in vacuo to provide 4.15 g of light orange solid. This material is dissolved in 20 mL of DCM. This material is purified utilizing an ISCO Companion with an 80 g cartridge of silica. The gradient is 5% EtOAc in heptanes for 4 column volumes followed by a linear gradient to 60% EtOAc in heptanes over 10 column volumes. 14 mL fractions of UV active elutant are collected. Fractions 6 through 14 are combined and evaporated in vacuo. This yields 2.04 g white solid (2.04 g, 88%).

Provenance & Evidence