4-Bromo-2-methoxybenzoic acid

Pale yellow liquid

Preparation 41; 4-Bromo-2-methoxybenzoic acid; Methyl iodide (861 μL, 13.83mmo.) was added to a mixture of 4-bromo-2-hydroxybenzoic acid [(1.2g, 5.53mmol), J. Med. Chem. 1997, 40, 2843] and potassium carbonate (2.3g, 16.59) in NA mixture of Compound I (3.0 g), 2N aqueous lithium hydroxide solution (18 mL) and methanol (55 mL) was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added water, and the mixture was extracted with diisopropylether. The aqueous layer was acidified with 4N hydrochloric acid, and extracted with chloroform. The chloroform layer was dried over magnesium sulfate, and then concentrated under reduced pressure to give Compound II (2.74 g)b b) N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (13.9 g, 72.7 mmol) and then TEA (12.2 g, 121 mmol) were added to a 0 C. solution of Propylphosphonic anhydride (10.4 mL, 17.46 mmol) was added to a stirred solution of trifluoroethylamine (0.93 mL, 11.64 mmol).General procedure: 1-chloro-/V, /V, 2-trimethylprop-1-en-1 -amine (2 eq.) was added to a solution of appropriate acid (1 eq.) in DCM (20 volumes). The reaction mixture was stirred at RT for 2 hrs. The reaction mixture was concentrated in vacuo and the residue dissolved in DCM (20 volumes) before addition of DIPEA (3 eq.) and the appropriate amine (1 eq). The reaction mixture was stirred at RT for 2 hrs. An aqueous work up was performed and the crude product was purified by normal phase chromatography, reverse phase chromatography or trituration from an appropriate solvent.

Molecular Weight:231.04
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:229.95786
Monoisotopic Mass:229.95786
Topological Polar Surface Area:46.5
Heavy Atom Count:12
Complexity:172
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes