m,alpha-Dichlorotoluene → 1-(3-Chloro-benzyl)-3-(4-methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one

Participants

Reaction Steps

Experimental conditions analogous to those described for Step 3 of Example 1 were used with 120 mg (0.390 mmol) of 3-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one, 75.2 mg (0.467 mmol) of 3-chlorobenzyl chloride, 19 mg (0.467 mmol, 60% dispersion in oil), and 1 mL of N,N dimethylformamide. The solid was collected by filtration and was purified by flash column chromatography using a gradient of 20-100% ethyl acetate in hexane to yield 65.7 mg of 1-(3-Chloro-benzyl)-3-(4-methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one. LC-MSD, m/z for C25H21ClN2O3 [M+H]: 433.12 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.5 min.

Provenance & Evidence