1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3-fluoro-4-methoxy-benzoyl)-7-trifluoromethyl-1H-[1,8]naphthyridin-4-one

Participants

Reaction Steps

Experimental conditions analogous to those described for Step 6 of Example 60, from 80 mg of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide, 2 mL of THF was treated with 3-fluoro-4-methoxyphenyl magnesium chloride (0.5 M in THF, 1.3 mL, 2 equiv) at rt for 2 h. The reaction was quenched by slow addition of saturated aqueous ammonium chloride. The mixture was subjected to HPLC and then preparative TLC purification to give 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3-fluoro-4-methoxy-benzoyl)-7-trifluoromethyl-1H-[1,8]naphthyridin-4-one. LCMS (ES) M+H 536.0.

Provenance & Evidence