Sodium Carbonate → HCID 178467438, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of the compound prepared in Example 336 (0.028 g), 1H-pyrazol-3-ylboronic acid (0.013 g) and tetrakis(triphenylphosphine)palladium (0.003 g) in dimethyl ether (0.3 mL) was added a solution of sodium carbonate (0.016 g) in water (0.1 mL). Argon was bubbled through the mixture for 10 minutes. The mixture was then heated at 95° C. for 8 hours. An additional tetrakis(triphenylphosphine)palladium (4.5 mg) and 1H-pyrazol-3-ylboronic acid (13 mg) were added, and the reaction mixture was again purged with argon for 10 minutes and then heated at 110° C. for 6 hours. An additional tetrakis(triphenylphosphine)palladium (10 mg) was added, and the reaction mixture was again purged with argon and then heated at 110° C. for another 38 hours. The reaction mixture was diluted with water and then filtered. The solid was purified by column chromatography on silica gel (dichloromethane:methanol=94:6) to obtain the title compound (2 mg) having the following physical data.

Provenance & Evidence