ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

Step 2: synthesis of ethyl 5-chloro-lH-pyrrolo[2, 3-c]pyridine-2-carboxylate 10-bTo a solution of ethyl 3-(2-chloro-5-nitropyridin-4-yl)-2-oxopropanoate 10-a (2.726 g, 10 mmoles) in THF (80 mL) and EtOH (30 mL) was added a saturated solution of ammonium chloride (50 mL). Then, iron (2.747 g, 4.9 eq) was added portionwise under vigorous stirring to the mixture at room temperature, which was subsequently heated at reflux for 2h. The mixture was cooled down to RT, filtered over dicalite and washed with warm THF/ethanol 1/1. The filtrate was evaporated and the residue was stirred and refluxed in 100 mL water. The resulting precipitate was filtered off hot, washed twice with warm water and then dried in vacuo to provide 1.9 g (84percent yield) of the targeted compound 10-b. m/z = 225 (M+H)+; 1H MR (400 MHz, OMSO-dPotassium (1(at))-1-(2-chloro-5-nitropyridin-4-yl)-3-ethoxy- 3-oxoprop-l-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, 19percent) as a brown solid: mp 170-175°C dec.;

Molecular Weight:224.64
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:224.0352552
Monoisotopic Mass:224.0352552
Topological Polar Surface Area:55
Heavy Atom Count:15
Complexity:250
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes