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Step B: fert-Butyl Ethyl (6-Nitropyridin-3-vDpropanedioate To a suspension of NaH (60 percent in oil, 0.65 g, 16 mmol) in DMF (40 mL) was added tert-butyl ethyl propanedioate (2.8 g, 15 mmol) at room temperature. The mixture was stirred for 30 min. A solution of <strong>[52092-47-4]5-chloro-2-nitropyridine</strong> (2.0 g, 13 mmol) in DMF (10 mL) was added. The mixture was heated to 80 °C and stirred for 4 hours. The solvent was removed under reduce pressure. Water was added and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04, concentrated and the residue was purified by column chromatography with silca gel to give tert-butyl ethyl (6-nitropyridin-3- yl)propanedioate. 1H-NMR (400MHz, CDC13) delta 8.58 (s, 1H), 8.20-8.27 (m, 2H), 4.69 (s, 1H), 4.21-4.26 (m, 2H), 1.45 (s, 9H), 1.28 (t, J= 7.2Hz, 2H).
Step B: fert-butyl ethyl (6-nitropyridin-3-yl)propanedioate: To a suspension of NaH (60 percent in oil, 0.650 g, 16.4 mmol) in DMF (40 mL) was added tert-butyl ethyl propanedioate (2.8 g, 15.1 mmol) at room temperature. The mixture was stirred for 30 min. A solution of 5-chloro-2- nitropyridine (2.00 g, 12.6 mmol) in DMF (10 mL) was added. The mixture was heated to 80 °C and stirred for 4 hours. The solvent was removed under reduce pressure. Water was added and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04, concentrated and the residue was purified by column chromatography with silca gel to give tert-butyl ethyl (6-nitropyridin-3-yl)propanedioate.
Step B: tert-butyl ethyl (6-nitropyridin-3-yl)propanedioate: To a suspension of NaH (60 percent in oil, 0.650 g, 16.4 mmol) in DMF (40 mL) was added tert-butyl ethyl propanedioate (2.8 g, 15.1 mmol) at room temperature. The mixture was stirred for 30 min. A solution of 5-chloro-2- nitropyridine (2.00 g, 12.6 mmol) in DMF (10 mL) was added. The mixture was heated to 80 °C and stirred for 4 hours. The solvent was removed under reduce pressure. Water was added and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2S04, concentrated and the residue was purified by column chromatography with silca gel to give tert-butyl ethyl (6-nitropyridin-3-yl)propanedioate.
With sodium hydride; trifluoroacetic acid; In N,N-dimethyl-formamide; mineral oil; at 80℃; for 4.5h;
[0218] To a suspension of NaH (60 percent in oil, 0.65 g, 16 mmol) in DMF (40 mL) was added tert-butyl ethyl propanedioate(2.8 g, 15 mmol) at room temperature. The mixture was stirred for 30 min. A solution of <strong>[52092-47-4]5-chloro-2-nitropyridine</strong> (2.0 g,13 mmol) in DMF (10 mL) was added. The mixture was heated to 80 °C and stirred for 4 hours. The solvent was removedunder reduce pressure. Water was added and the mixture was extracted with EtOAc. The combined organic layer waswashed with brine, dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatographywith silca gel to give tert-butyl ethyl (6-nitropyridin-3-yl)propanedioate. 1H-NMR (400MHz, CDCl3) delta 8.58 (s, 1H),8.20?8.27 (m, 2H), 4.69 (s, 1H), 4.26?4.26 (m, 2H), 1.45 (s, 9H), 1.28 (t, J = 7.2Hz, 2H).
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