4-Chloro-N-methoxy-N-methylbenzamide → 3-(4-chloro-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

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A −78° C. solution of 3-iodo-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one (113 mg, 0.3 mmol, 1 equiv) in 3 mL of THF was treated with 1.65 mL of isopropyl magnesium chloride (1.1 equiv) for 2 hours. Then 4-chloro-N-methoxy-N-methyl-benzamide (46 μL, 1.2 equiv) was added and stirring continued at rt for 2 hours. The reaction was quenched by slow addition of saturated aqueous solution of NH4Cl. Standard workup followed by HPLC purification gave 3-(4-chloro-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one. LCMS (ES) M+H 389.1

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