1H-Indole-3-carboxylic acid, 5-chloro-, methyl ester

General procedure: To a solution of compounds 21(b-c) (1 equiv) in MeOH, a solution of KOH in water was added. The reaction mixture was refluxed for 3 h. The solvents were removed under reduced pressure, the residue was partitioned between EtOAc and 1 N aq. HCl and the layers were separated. The aqueous layer was washed with EtOAc (3×) and the combined organic phases were washed with brine (1×), dried over anhydrous Na2SO4, filtered and concentrated to near dryness. The crude residue was purified by silica gel flash column chromatography eluted with mixtures of MeOH in dichloromethane to afford the corresponding methyl esters 22(b-c).

Molecular Weight:209.63
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:209.0243562
Monoisotopic Mass:209.0243562
Topological Polar Surface Area:42.1
Heavy Atom Count:14
Complexity:234
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes