Sodium Carbonate → HCID 86652292, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the crude Compound 10 (12.5 g, prepared from 15.1 g of Compound 9 using a similar procedure described earlier for the synthesis of Compound 10), 3,6-dichloropyridazine (5.60 g, 37.6 mmol), and sodium carbonate solution (40 mL. 2M, 80.0 mmol) in DMF (25 mL) was degassed with argon. To this mixture was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (2.6 g, 3.1 mmol). The resulting mixture was degassed with argon and then heated at 90° C. for 3 h. After cooling, the solution was quenched by adding water. The solution was extracted into dichloromethane (3×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by column chromatography (100:0 to 0:100 hexanes/ethyl acetate) provided the Compound 31 as a light-red solid (6.23 g, 51%); 1H NMR (500 MHz, CDCl3) δ 8.29 (d, J=9.0 Hz, 1H), 7.99 (d, J=9.0 Hz, 2H), 7.88-7.83 (m, 4H), 7.79 (s, 1H), 7.50-7.47 (m, 2H), 7.38 (dd, J=8.5, 1.5 Hz, 1H), 7.00 (d, J=0.8 Hz, 1H), 5.00-4.90 (m, 1H), 4.50-4.40 (m, 1H), 4.25-4.15 (m, 1H), 3.60-3.50 (m, 1H), 3.15-3.05 (m, 1H), 2.84 (s, 3H). ESI MS m/z 386 [M+H]+.

Provenance & Evidence