1-Butanol → N-(2-Chloro-5-(4-(pyridin-3-yl)quinolin-6-yl)pyridin-3-yl)methanesulfonamide

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To a 5 mL microwave vial, N-(2-chloro-5-(4-chloroquinolin-6-yl)pyridin-3-yl)methanesulfonamide (0.0500 g, 0.136 mmol, Example 9), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.0334 g, 0.163 mmol), potassium acetate (0.0333 g, 0.339 mmol) and dichlorobis(di-tert-butylphenylphosphine)palladium(II) (0.0042 g, 0.0068 mmol) were mixed into 1 mL of nBuOH along with 0.1 mL of water. The reaction mixture was stirred at 105° C. for 3 h. The reaction mixture was partitioned between water (10mL)/brine (10 mL) and 25% IPA/CHCl3 (20 mL). The aqueous phase was extracted with 25% IPA/CHCl3 (2×20 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (eluent: acetone in DCM 20%-70%) to afford an off white solid (0.0286 g) as the desired product. MS (ESI pos. ion) m/z calcd for C20H15ClN4O2S: 410.1; found 410.9 [M+1]. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.85 (s, 1 H) 9.05 (d, J=4.38 Hz, 1 H) 8.86 (d, J=1.75 Hz, 1 H) 8.77 (dd, J=4.82, 1.61 Hz, 1 H) 8.63 (d, J=2.34 Hz, 1 H) 8.24-8.33 (m, 1 H) 8.09-8.24 (m, 3 H) 8.05 (d, J=1.75 Hz, 1 H) 7.59-7.69 (m, 2 H) 3.16 (s, 3 H).

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