Sodium Bicarbonate → 5-(3-Chlorophenyl)-4-(3-cyano-4-fluorophenyl)-1,3-thiazole-2-carboxylic acid

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Reaction Steps

At room temperature, 231 mg (1.48 mmol) of (3-chlorophenyl)boronic acid are added to 350 mg (0.985 mmol) of the compound from Example 29A and 56.9 mg (0.049 mmol) of tetrakis(triphenylphosphine)palladium in 26 ml of DME. 252 mg (3.01 mmol) of sodium bicarbonate in 11 ml of water are subsequently added, and the mixture is stirred under reflux for 1 h. The reaction solution is subsequently concentrated under reduced pressure and the residue is taken up in ethyl acetate and washed with a saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated. The residue is purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). 353 mg (100% of theory) of the title compound are obtained.

Provenance & Evidence