6-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID

A suspension of 6-bromo-4-hydroxy-quinoline-3-carboxylic acid ethyl ester (102.59 g, 337.7 mmol) in 10percent potassium hydroxide in water (689 mL) was heated to reflux for 5 h to afford a light brown solution. Ethyl 6-bromo-4-hydroxy-3-quinolinecarboxylate (3.0 g, 10 mmol) was added to NaOH 10percent (40 mL)Should be heated to reflux for 1 hour. The reaction solution was cooled to ° C and adjusted to pH 1 with hydrochloric acid (10 N). Filtration, filter residue washed with water, dried 2.6g(96percent) of a white solid.4.1.6 10558] The bicyclic compound 3-2 is prepared from bromoaniline 3-1 using diethyl 2-(ethoxymethylene)malonate or a similar reagent. Deprotection and removal of the carboxylic acid, followed by halogenation using a reagent such as phosphorus oxychloride yields compound 3-5. Derivatization with pyridine boronate in Suzuki coupling conditions yields 3-6, which is reacted in a second Suzuki reaction with a benzothiazolyl boronate to yield compound 3-7. Subsequent heating in hydrochloric acid in a solvent such as methanol results in removal of an acetyl group.

Molecular Weight:268.06
XLogP3:2.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:266.95311
Monoisotopic Mass:266.95311
Topological Polar Surface Area:66.4
Heavy Atom Count:15
Complexity:340
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes