Sodium Carbonate → HCID 44124753, compound

Participants

Reaction Conditions

Reaction Steps

To a 25-mL, round-bottomed flask was added N-(5-bromopyridin-3-yl)-4-fluorobenzenesulfonamide (0.15 g, 0.45 mmol), bis(pinacolato)diboron (0.17 g, 0.68 mmol), potassium acetate (0.18 g, 1.8 mmol) and 1,4-dioxane (4.0 mL). The mixture was carefully evacuated and backfilled with N2. To this mixture was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)dichloromethane adduct (0.033 g, 0.045 mmol, Strem Chemicals, Inc., Newburyport, Mass.). The mixture was carefully evacuated and backfilled with N2. The mixture was stirred at 90° C. for 19 h then allowed to cool to room temperature. To the solution was added DMF (4.0 mL), N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide (Example 1, Step 4) (0.075 g, 0.36 mmol) and aq. Na2CO3 (0.89 mL, 1.8 mmol, 2 M). The mixture was carefully evacuated and backfilled with N2. To the mixture was added trans-dichlorobis(triphenylphosphine)palladium (II) (0.025 g, 0.036 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 2 h and then was allowed to cool to room temperature. The solution was poured into water (100 mL), extracted with 25% iPrOH/CHCl3 (3×75 mL) and the combined extracts were washed with brine, dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (2 to 8% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a tan solid. MS (ESI pos. ion) m/z: 427 (M+1). 1H NMR (400 MHz, DMSO-d6): δ 10.95 (s, 1H), 10.84 (s, 1H), 8.92 (d, J=1.8 Hz, 1H), 8.41 (d, J=2.5 Hz, 1H), 8.31 (s, 1H), 8.09-8.13 (m, 2H), 7.88-7.91 (m, 2H), 7.76 (d, J=9.4 Hz, 1H), 7.42 (d, J=8.8 Hz, 2H), 2.12 (s, 3H).

Provenance & Evidence