1,4-Dioxane → N-(7-(benzo[d][1,3]dioxol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide

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A suspension of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 50 mg, 0.151 mmol), benzo[d][1,3]dioxol-4-ylboronic acid (50 mg, 0.302 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (9 mg, 12 μmol) in 2:1 1,4-dioxane/saturated aqueous NaHCO3 (330 microliters of 1,4-dioxane and 670 microliters of saturated aqueous NaHCO3) was prepared in a 2 mL microwave reaction vessel and the sealed reaction vessel warmed to 110° C. for 20 minutes. The reaction mixture was cooled to rt, diluted with methanol, filtered, and purified via preparative HPLC, 5-95% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a yellow solid (2.8 mg, 4%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (s, 6 H) 5.20 (s, 1 H) 6.18 (s, 2 H) 6.57 (d, J=2.27 Hz, 1 H) 7.17 (d, J=8.34 Hz, 1 H) 7.56-7.69 (m, 3 H) 7.72 (d, J=1.77 Hz, 1 H) 7.98-8.10 (m, 3 H) 8.19 (d, J=2.27 Hz, 1 H) 11.23 (s, 1 H). ESI-MS: m/z 417.0 (M+H)+.

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