Sodium Carbonate → HCID 178474394, compound

Participants

Reaction Conditions

Reaction Steps

To a 25 mL round-bottomed flask was added N-(5-bromo-2-chloropyridin-3-yl)-4-fluorobenzenesulfonamide (0.150 g, 0.410 mmol) (Step 1, Example 48), bis(pinacolato)diboron (0.156 g, 0.615 mmol, Aldrich, St, Louis, Mo.), potassium acetate (0.161 g, 1.64 mmol) and 1,4-dioxane (4.0 mL). The mixture was carefully evacuated and backfilled with N2. To the solution was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloromethane adduct (0.030 g, 0.041 mmol, Strem Chemical, Inc., Newburyport, Mass.). The mixture was carefully evacuated and backfilled with N2 again. The mixture was stirred at 90° C. for 6 h. The reaction mixture was cooled to rt and to it was added DMF (4.0 mL), N-(5-bromo-1H-benzo[d]imidazol-2-yl)acetamide (0.080 g, 0.31 mmol) and aq sodium carbonate (0.79 mL, 1.6 mmol, 2 M). The mixture was carefully evacuated and backfilled with N2. To the mixture was added trans-dichlorobis(triphenylphosphine)palladium(II) (0.022 g, 0.031 mmol, Strem Chemical, Inc., Newburyport, Mass.). Once again the mixture was carefully evacuated and backfilled with N2. The mixture was stirred at 90° C. for 16 h and then, after cooling to rt, was poured into aq. NaCl (100 mL) and extracted with 25% iPrOH/CHCl3 (3×75 mL). The combined extracts were dried (Na2SO4) and concentrated. The material was then taken up in MeOH/CH2Cl2 and concentrated onto silica. Purification by silica gel chromatography (0.5 to 5.0% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a white solid (0.0217 g, 15%). MS (ESI, positive ion) m/z: 460 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.18 (s, 3H), 7.37 (br s, 1H), 7.44 (t, J=8.8 Hz, 2H), 7.56 (br s, 1H), 7.70 (br s, 1H), 7.83 (dd, J=8.8, 5.3 Hz, 2H), 7.91 (s, 1H), 8.56 (br s, 1H), 10.44 (br s, 1H), 11.62 (br s, 1H), 12.16 (br s, 1H).

Provenance & Evidence