Sodium Carbonate → 2-{[(4-Fluorophenyl)methyl]oxy}-N-3-pyridinyl-5-(4-pyridinyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}-N-3-pyridinylbenzamide (may be prepared as described in Example 59; 150 mg, 0.37 mmol) in 1,2-dimethoxyethane (5 ml) was added 4-pyridinylboronic acid (68.9 mg, 0.561 mmol), sodium carbonate (198 mg, 1.87 mmol) and bis(triphenylphosphine)palladium(II) chloride (15.74 mg, 0.02 mmol), followed by water (1 ml). The reaction was heated at 80° C. overnight. The reaction mixture was then placed in a microwave vial with another 0.5 eq of boronic acid and 5% catalyst and heated at 120° C. for 25 minutes. The solvent was removed in vacuo, redissolved in 1:1 DMSO/methanol and purified by MDAP to yield the title compound as white solid. 56 mg.

Provenance & Evidence