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With hydrogenchloride; sodium periodate In tetrahydrofuran; water at 20℃; for 3.5h;
(Pyridin-2-yl-amino) phenyl boronic acid B-1
toN- (pyridin-2-yl) -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzamide(2 g, 6.2 mmol) in a mixed solvent of THF: H20 (24 mL: 6 mL) was added NaIO4(3.27 g, 18.6 mmol),And stirred at room temperature for 30 minutes.2N HCl aqueous solution (1.65 mL) was added.It was stirred at room temperature for 3 hours.The mixture was diluted with ethyl acetate,Wash with brine.Separated and dried over anhydrous Na2SO4,Filter and concentrate.Purification by column chromatography using MeOH / DCM = 1: 10 gave 1.4 g of the compound (pyridin-2-ylcarbamoyl) phenylboronic acid,Yield: 93%.
93%
Stage #1: N-(pyridin-2-yl)-4-(4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide With sodium periodate In tetrahydrofuran; water at 20℃; for 0.5h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 3h;
(Pyridin-2-ylcarbamoyl) phenylboronic acid II-1
N- (pyridin-2-yl) -4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl) benzamide(2g, 6.2mmol) in a mixed solvent of THF: H2O (24mL: 6mL) was added NaIO4 (3.27g,18.6 mmol) and stirred at room temperature for 30 minutes. 2N aqueous HCl (1.65 mL) was added. It was stirred at room temperature for 3 hours. The mixture was diluted with ethyl acetate and washed with brine. Separate and dry with anhydrous Na2SO4, filter and concentrate.Purification by column chromatography using MeOH / DCM = 1: 10 gave the product (pyridin-2-ylcarbamoyl) phenylboronic acid II-1 (1.4 g, 93%).
7 Example 7: Synthesis of compound XlV-b
To a round-bottom flask was added compound IV (17.2 g), pinacol (12.6 g) and methanol (70 mL). The mixture was stirred for 2 h at 40~50 °C. The reaction mixture was cooled to 5 °C and stirred for 1 h. After filtration and drying, compound XlV-b was obtained as white solid (14.5 g, 63% yield).XH NMR (400 MHz, DMSO) δ 10.82 (s, 1H), 8.40 - 8.38 (m, 1H), 8.23 - 8.20 (m, 1H), 8.06 - 8.02 (m, 2H), 7.87 - 7.77 (m, 3H), 7.18 - 7.14 (m, 1H), 1.31 (s, 12H).
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