Sodium hydride → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-6,8-dimethyl-1H-[1,7]naphthyridin-4-one

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Reaction Steps

Experimental conditions analogous to described for Step 3 of Example 1 were used with 42 mg (0.137 mmol) of 3-(3,4-Dimethyl-benzoyl)-6,8-dimethyl-1H-[1,7]naphthyridin-4-one, 6 mg (0.165 mmol, 60% dispersion in oil) of sodium hydride, 41.3 mg (0.165 mmol) of 2-bromo-6-bromomethyl-pyridine and 1.5 mL of N,N-dimethylformamide. The crude brown solid was purified by flash column chromatography using 30-100% ethyl acetate in hexane to yield 7.9 mg of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-6,8-dimethyl-1H-[1,7]naphthyridin-4-one as an off white solid. LC-MSD, m/z for C25H22BrN3O2 [M+H]: 477.37 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.9 min

Provenance & Evidence