Sodium Carbonate → HCID 24994334, compound

Participants

Reaction Conditions

Reaction Steps

Alternative preparation: [4-(Methylsulfonyl)phenyl]boronic acid (0.17 g, 0.84 mmol) and 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 81, Step 1, 0.25 g, 0.70 mmol) were mixed with DME (4 mL) and 2M Na2CO3 (4 mL). The mixture was degassed with N2, then PdCl2(PPh3)2 (50 mg, 0.07 mmol) was added. The reaction mixture was degassed again with N2 and heated at 80° C. for 6 h, then cooled to ambient temperature, and diluted with EtOAc. The mixture was washed with water and brine and the organic layer was dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a brown solid. The crude product was purified by chromatography on a silica gel column eluted with 25% EtOAc/CH2Cl2 followed by trituration with hexane containing 1% of MeOH to give 0.245 g (81%) of the title compound as a white solid.

Provenance & Evidence