Potassium Carbonate → HCID 58229488, compound

Participants

Reaction Steps

To a microwave vial (5 mL) was added N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-fluorobenzenesulfonamide (0.129 g, 0.312 mmol), 6-bromoquinolin-3-ol (Li et. Al, Bioorganic & Medicinal Chemistry Letters (2006), 16(7), 2000-2007) (0.0703 g, 0.314 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.0128 g, 0.0156 mmol) and potassium carbonate (2.0 M, 0.390 mL, 0.781 mmol) in 1,4-dioxane (3 mL). The mixture was degassed by bubbling nitrogen through for 10 min. The tube was irradiated with microwave at 100° C. for 10 min. The reaction mixture was cooled to RT then partitioned between water (10 mL) and EtOAc (10 mL). The product went into aqueous almost exclusively. The aqueous phase was passed through BE-SCX column (Varian, Palo Alto, Calif., 10 gm) then eluted with MeOH. MeOH fraction contains the product. MeOH was evaporated and yielded a brown solid (0.0846 g) as the desired product. m/z: calc'd for C20H13ClFN3O3S: 429.0; found 430.0 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 7.21-7.35 (m, 2 H), 7.52-7.65 (m, 2 H), 7.74-7.86 (m, 3 H), 7.89 (d, J=1.8 Hz, 1 H), 7.96 (d, J=8.6 Hz, 1 H), 8.03-8.15 (m, 1 H), 8.58 (d, J=2.8 Hz, 1 H), 10.40 (s, 1 H).

Provenance & Evidence