(5-chloro-2-ethoxycarbonylphenyl)boronic acid

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Amino-3-bromopyridine (87 mg, 0.50 mmol), 5-chloro-2-ethoxycarbonylphenylboronic acid (149 mg, 0.65 mmol), palladium(II) acetate (5 mg, 0.02 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (16 mg, 0.04 mmol), and potassium carbonate (207 mg, 1.50 mmol) were dissolved in dioxane/H2O (1.65 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was concentrated, suspended in EtOAc/H2O, and filtered. The precipitate was washed with EtOAc/H2O, and dried under vacuum to provide 5 (29 mg, 25% yield) as a solid. LC-MS (M+H=231, obsd.=231). 1H NMR (400 MHz, d6-DMSO): δ 12.18 (s, 1H), 8.91 (dd, 1H), 8.68 (d, 1H), 8.54 (dd, 1H), 8.32 (d, 1H), 7.74 (dd, 1H), 7.34 (dd, 1H). The reaction mixture was concentrated filtered The precipitate was washed with EtOAc/H2O dried under vacuum

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Amino-3-bromopyridine (87 mg, 0.50 mmol), 5-chloro-2-ethoxycarbonylphenylboronic acid (149 mg, 0.65 mmol), palladium(II) acetate (5 mg, 0.02 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (16 mg, 0.04 mmol), and potassium carbonate (207 mg, 1.50 mmol) were dissolved in dioxane/H2O (1.65 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was concentrated, suspended in EtOAc/H2O, and filtered. The precipitate was washed with EtOAc/H2O, and dried under vacuum to provide 5 (29 mg, 25% yield) as a solid. LC-MS (M+H=231, obsd.=231). 1H NMR (400 MHz, d6-DMSO): δ 12.18 (s, 1H), 8.91 (dd, 1H), 8.68 (d, 1H), 8.54 (dd, 1H), 8.32 (d, 1H), 7.74 (dd, 1H), 7.34 (dd, 1H). The reaction mixture was concentrated filtered The precipitate was washed with EtOAc/H2O dried under vacuum

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Amino-3-bromopyridine (87 mg, 0.50 mmol), 5-chloro-2-ethoxycarbonylphenylboronic acid (149 mg, 0.65 mmol), palladium(II) acetate (5 mg, 0.02 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (16 mg, 0.04 mmol), and potassium carbonate (207 mg, 1.50 mmol) were dissolved in dioxane/H2O (1.65 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was concentrated, suspended in EtOAc/H2O, and filtered. The precipitate was washed with EtOAc/H2O, and dried under vacuum to provide 5 (29 mg, 25% yield) as a solid. LC-MS (M+H=231, obsd.=231). 1H NMR (400 MHz, d6-DMSO): δ 12.18 (s, 1H), 8.91 (dd, 1H), 8.68 (d, 1H), 8.54 (dd, 1H), 8.32 (d, 1H), 7.74 (dd, 1H), 7.34 (dd, 1H). The reaction mixture was concentrated filtered The precipitate was washed with EtOAc/H2O dried under vacuum