Potassium Carbonate → Ethyl (1-benzyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-4-yloxy)acetate

Participants

Reaction Steps

A mixture of 1-benzyl-2-methyl-1H-pyrrolo[2,3-b]pyridin-4-ol 7 (0.30 g, 1.26 mmol), 2-bromoethylacetate (1.05 g, 6.29 mmol) and K2CO3 (2.0 g) in anhydrous acetone (15 mL) were heated at reflux for 6 h under N2. After cooling, the mixture was filtered through celite and the filtrate was concentrated to yield a syrup. It was then re-dissolved in ethyl acetate and washed with water (10×2 mL), brine and dried (Na2SO4). The solvent was removed under reduced pressure, and the residue was chromatographed on a silica gel column eluting with 40% ethylacetate in hexanes afforded the title compound 8 as an amorphous white solid. Yield: 0.25 g, 61%; ESI MS: m/z 325.0 (M+1).

Provenance & Evidence