[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([NH:16][CH3:17])=[O:15])=[CH:12][N:11]=[C:10]([CH3:18])[CH:9]=2)=[C:4](F)[CH:3]=1.[H-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](=[CH:12][N:11]=[C:10]([CH3:18])[CH:9]=3)[C:14](=[O:15])[N:16]([CH3:17])[C:4]=2[CH:3]=1To a solution of 4-(4-chloro-2-fluorophenyl)-N,6-dimethylnicotinamide (520 mg, 1.86 mmol) in tetrahydrofuran (20 mL) at 0° C. was added NaH (224 mg, 5.60 mmol). The reaction mixture was brought to room temperature gradually and stirred at room temperature for 15 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to afford product, 8-chloro-2,6 dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (480 mg, 1.51 mmol, 81% crude yield) as a red solid. The material was carried forward without further purification. LC/MS (ESI) m/e 259.0 [(M+H)+, calcd for C14H12ClN2O 259.0]; LC/MS retention time (Method C): tR=1.74 min. 1H NMR (300 MHz, METHANOL-d4) δ ppm 9.41 (s, 1H), 8.48 (d, J=8.59 Hz, 1H), 8.23 (s, 1H), 7.69 (d, J=1.98 Hz, 1H), 7.44 (dd, J=8.64, 1.94 Hz, 1H), 3.78 (s, 3H), 2.75 (s, 3H).
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