Benzoic acid, 5-bromo-2-[(methylsulfonyl)amino]-, methyl ester synthesis

Yield:452350-33-3 95%

Reaction Conditions:

with pyridine in dichloromethane at 20;

Steps:

Intermediate 108To a solution of methyl 2-amino-5-bromobenzoate (7.38 g, 32.0 mmol) and pyridine (6.3 mL, 81.5 mmol) in 100 mL of anhydrous CH₂CL₂, was added slowly methane sulfonylchloride (6.5 mL, 79.9 mmol). After stirring overnight, reaction mixture was quenched with 100 mL of IN HC1 _(aq₎. Aqueous mixture was extracted with ethyl acetate (3x120 mL) and combined organic layers were washed 200 mL brine. Organics were dried (MgS0₄), filtered, and concentrated under reduced pressure to yield intermediate 108 as an off white solid. Silica gel column chromatography (0-30% Ethyl Acetate in Hexanes), yielded intermediate C-C (9.35 g, 95 %) as a white off- white solid.¹ H-NMR (CDC1₃, 300 MHz): δ 10.4 (s, IH), 8.22 (s, IH), 7.63 (s, 2H), 3.96 (s, 3H), 3.05 (s, 3H) LCMS m/z [M+H]⁺ C₉Hi₀BrNO₄S requires: 307.95. Found 308.06

References:

WO2011/163518,2011,A1 Location in patent:Page/Page column 299-300