Water → N-(2-Chloro-5-(3-(pyridin-4-yl)quinoxalin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a 5 mL microwave vial, N-(2-chloro-5-(3-chloroquinoxalin-6-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (0.106 g, 0.236 mmol), pyridine-4-ylboronic acid (0.0430 g, 0.350 mmol), dichlorobis(di-tert-butylphenylphosphine)palladium(II) (0.0111 g, 0.0178 mmol), potassium acetate (0.0581 g, 0.592 mmol) and water (0.300 ml, 16.7 mmol) were mixed into (4 mL). The mixture was degassed by bubbling nitrogen through for 5 min. The reaction mixture was stirred at 90° C. for 6 h, then at 110° C. for 1.5 h. The reaction mixture was partitioned between Tris-1M HCl pH 7 buffer (20 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (20 mL). The combined organic phases were washed with saturated aqueous NaCl (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (eluent: acetone in DCM 0%-50%) to afford a light yellow solid (0.0662 g) as the desired product. MS (ESI pos. ion) m/z calcd for C24H15ClFN5O2S: 491.1; found 491.9 [M+1]. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.06-7.23 (m, 3 H) 7.82-7.92 (m, 2 H) 8.01 (dd, J=8.77, 2.05 Hz, 1 H) 8.14 (dd, J=4.53, 1.61 Hz, 2 H) 8.31 (d, J=8.77 Hz, 1 H) 8.40 (t, J=1.83 Hz, 2 H) 8.57 (d, J=2.34 Hz, 1 H) 8.89 (dd, J=4.68, 1.46 Hz, 2 H) 9.42 (s, 1 H).

Provenance & Evidence