Diisopropylethylamine → HCID 86716104, compound

Participants

Reaction Conditions

Reaction Steps

Into a 250-mL round-bottom flask was placed a solution of methyl 2-amino-5-bromobenzoate (5 g, 21.73 mmol, 1.00 equivalent), 2-(pyridin-2-yl)acetic acid hydrochloride (4.5 g, 25.92 mmol, 1.20 equivalent), HATU (10 g, 26.30 mmol, 1.20 equivalents), and DIEA (8.5 g, 65.77 mmol, 3.00 equivalents) in N,N-dimethylformamide (100 mL). After stirring overnight at 20° C., the reaction was quenched with 100 mL of water and extracted with 3×100 mL of dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was applied onto a silica gel column eluted with dichloromethane/methanol (1:50) to give the title compound as a red solid.

Provenance & Evidence