Diisopropylethylamine → HCID 59314205, compound

Participants

Reaction Steps

To a 40 mL vial containing a stirring bar, 5-chloro3-methyl-benzo[b]thiophene-2-carboxylic acid ([50451-84-8], 0.81 g, 3.53 mmol) is charged with dry DCM (10 mL). Stirring is initiated. HBTU (1.34 g, 3.54 mmol) and the DIPEA (1.4 mL, 8.0 mmol) are added. The 2-aminoindane-2-carboxylic acid ethyl ester (0.725 g, 3.53 mmol) is added. The reaction is allowed to stir for 240 h. Analysis by tlc of the reaction mixture (silica, 10% MeOH/DCM) indicates complete consumption of the starting amine. The contents of the reaction flask are diluted with EtOAc (80 mL) and transferred to a reparatory funnel. This is washed consecutively with dilute aqueous NaHCO3 (25 mL) and brine (25 mL), dried over MgSO4, filtered and evaporated in vacuo to provide 1.26 g of a off white solid. This material is purified utilizing an ISCO Companion with a 40 g cartridge of silica. The gradient is 20% EtOAc in heptanes over 3 column volumes followed by a step gradient to 30% and then 50% and then 70% EtOAc for 2 column volumes each with a ramp of 1 column volume. 25 mL fractions are collected. Fractions 22 through 60 are combined and evaporated in vacuo. Pumping to a constant weight gives amorphous white solid 0.78 g.

Provenance & Evidence