HCID 86619045, compound → Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Potassium (1Z)-1-(2-chloro-5-nitropyridin-4-yl)-3-ethoxy-3-oxoprop-1-en-2-olate (2.86 g, 9.20 mmol) was dissolved in acetic acid (140 mL) and iron powder (2.11 g, 37.7 mmol) was added. The mixture was heated at 60° C. for 6 h. The mixture was filtered through a pad of diatomaceous earth and washed with water followed by ethanol. The filtrate was concentrated to dryness. The residue was dissolved in 1:1 methylene chloride/methanol, filtered through a bed of silica gel and washed with 1:1 ethyl acetate/methylene chloride until the filtrate was no longer UV-active. Concentration of the filtrate provided ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (0.39 g, 19%) as a brown solid: mp 170-175° C. dec.; 1H NMR (300 MHz, CD3OD) δ1.42 (3H, t, J=7.1 Hz), 4.44 (2H, q, J=7.1 Hz), 7.17 (1H, s), 7.72 (1H, s), 8.60 (1H, s); ESI MS m/z 225 [C10H9ClN2O2+H]+; HPLC (Method A) 94.9% (AUC), tR=18.1 min.

Provenance & Evidence