Cesium carbonate → 3'-({[4-Bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)-5-fluorobiphenyl-3-carboxylic acid

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Reaction Steps

[3-({[4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-yl]oxy}methyl)phenyl]boronic acid (3-1) (400 mg, 0.957 mmol, 1.0 equiv.), 3-bromo-5-fluorobenzoic acid (12) (800 mg, 3.65 mmol, 3.8 equiv.) and dichloro[1,1′-bis (diphenylphosphino) ferrocene] palladium II dichloromethane adduct (78 mg, 0.096 mmol, 0.1 equiv.) were dissolved in anhydrous degassed 1,4-dioxane (8 mL), then treated with a 1 M aqueous solution of cesium carbonate (5.2 mL, 5.3 mmol, 5.5 equiv.). The reaction mixture was irradiated in microwavereactor at 150° C. for 10 minutes. The mixture was concentrated in vacuo and purified by reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present) to afford Example 3-2. 1H NMR δ (CDCl3): 8.15 (s, 1H), 7.77 (s, 2H), 7.58-7.52 (m, 4H), 7.41 (d, 1H, J=8.5 Hz), 7.29 (d, 1H, J=9.0 Hz), 5.32 (s, 2H), 4.38 (s, 2H), 1.04 (s, 9H) ppm. LRMS m/z (M+H) 512.0 and 514.0 (intensity ratio ˜1:1) found, 512.1 and 514.1 required.

Provenance & Evidence