Diisopropylethylamine → HCID 11180570, compound

Participants

Reaction Steps

Ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate (0.23 g, 0.67 mmol) was dissolved in 7 mL of methylene chloride. To the solution was added diisopropylethylamine (0.5 mL, 2.9 mmol) and 4-trifluoromethoxy-benzenesulfonyl chloride (0.13 g, 0.5 mmol). After being stirred at room temperature overnight the reaction was concentrated and the residue was re-dissolved in 10 mL of 2:1:1 THF/MeOH/water. Lithium hydroxide monohydrate (0.15 g, 3.6 mmol) was added and the mixture was stirred at 40° C. overnight. Most of the organic solvents was removed and the reaction mixture was made acidic (pH 6) with glacial acetic acid, and the solid was collected and purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min). The product was collected based on UV absorption and concentrated to give the title compound as a pale yellow solid (0.16 g, 45%):

Provenance & Evidence