Magnesium bromide 2,3-dihydro-1,4-benzodioxin-6-ide (1/1/1) → 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-6,7-dimethyl-1-(6-methyl-pyridin-2-ylmethyl)-1h-[1,8]naphthyridin-4-one

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Reaction Steps

Experimental conditions analogous to those described for Step 6 of Example 60 were used with 100 mg (0.273 mmol) of 6,7-Dimethyl-1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl amide, 1.2 mL (0.60 mmol, 0.5M solution in tetrahydrofuran) of 3,4-(ethylenedioxy)phenylmagnesium bromide, and 1 mL of THF. The crude product was purified by flash column chromatography using 20-100% ethyl acetate in hexane and further purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to afford 42.7 mg of 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-6,7-dimethyl-1-(6-methyl-pyridin-2-ylmethyl)-1H-[1,8]naphthyridin-4-one. LC-MSD, m/z for C26H23N3O4 [M+H]: 442.17 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 1.9 min.

Provenance & Evidence