N,N'-Dimethylethylenediamine → methyl 4-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-1-methyl-6-(2-pyridylmethoxy)pyrrolo[2,3-b]pyridine (0.5 g, 1.57 mmol) in 1,4-dioxane (10 mL) is added methyl 3-oxopiperazine-1-carboxylate (0.271 g, 1.88 mmol) and potassium phosphate (0.467 g, 2.20 mmol). The mixture is degassed with nitrogen for 15 minutes, then copper(I) iodide (0.060 g, 0.31 mmol) and N,N′-dimethylethylenediamine (0.055 g, 0.63 mmol) are added. The reaction vessel is sealed and heated at 100° C. for 16 h. The reaction is cooled to room temperature, quenched with water (50 mL) and extracted with EtOAc (3×100 mL). The combined organic layers are dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue is purified by column chromatography on neutral alumina, eluting with 1% MeOH in DCM. The resultant product is triturated with Et2O/pentane (1:1) to afford the title compound (0.5 g, 1.26 mmol) as an off white solid. MS (m/z): 396 (M+1). 1H-NMR (400 MHz, DMSO-d6): δ 3.66 (s, 3H), 3.68 (s, 3H), 3.75 (m, 4H), 4.14 (s, 2H), 5.49 (s, 2H), 6.66 (d, 1H), 7.30-7.33 (m, 2H), 7.50 (d, 1H), 7.77-7.82 (m, 2H), 8.56 (d, 1H).

Provenance & Evidence