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10.i. 7-chloro-3-fluoro-1,8-naphthyridin-2(1H)-one To a solution of <strong>[127446-34-8]N-(6-chloro-3-formylpyridin-2-yl)pivalamide</strong> (prepared as described in J. Org. Chem. (1990), 55, 4744; 3.0 g, 12.64 mmol) in MeCN (250 mL) was added triethyl 2-fluoro-phosphonoacetate (4 g, 16.51 mmol), lithium chloride (0.935 g) and DBU (2.8 mL, 18.7 mmol). The mixture was stirred at rt for 4 h. The solvent was evaporated and the residue was partitioned between 1N HCl (100 mL) and ether (150 mL). The aq. layer was extracted with ether (100 mL) and the combined ethereal layers were dried over Na2SO4, filtered and concentrated to dryness. The residue was taken up in dioxane (15 mL) and 6N HCl (50 mL) was added. The mixture was heated to reflux for 90 min. The mixture was cooled to 0 C. and the volatiles were removed in vacuo. The solids were filtered off and washed with water. The solid was dried in vacuo to afford the title compound as a yellow solid (1.38 g, 56% yield). The title compound was only 70% pure. MS (ESI, m/z): 199.1 [M+H+] for C8H4N2OClF.
To a solution of Lambda/-(6-chloro-3-formylpyridin-2-yl)pivalamide (prepared as described in J. Org. Chem. (1990), 55, 4744; 3.0 g, 12.64 mmol) in MeCN (250 niL) was added triethyl 2-fluoro-phosphonoacetate (4 g, 16.51 mmol), lithium chloride (0.935 g) and DBU (2.8 mL, 18.7 mmol). The mixture was stirred at rt for 4 h. The solvent was evaporated and the residue was partitioned between N HCl (100 mL) and ether (150 mL). The aq. layer was extracted with ether (10O mL) and the combined ethereal layers were dried over Na2SO4, filtered and concentrated to dryness. The residue was taken up in dioxane (15 mL) and 6JV EtaC1 (50 mL) was added. The mixture was heated to reflux for 90 min. The mixture was cooled to 00C and the volatiles were removed in vacuo. The solids were filtered off and washed with water. The solid was dried in vacuo to afford the title compound as a yellow solid (1.38 g, 56% yield). The title compound was only 70% pure. MS (ESI, m/z): 199.1 [M+Eta+] for C8H4N2OClF.
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