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With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 140℃; for 2h;
Step C: rac-(6-Fluoro-2,3-dihydro-benzofuran-3-yl)-(6-nitro-quinolin-2-yl)-amine A mixture of <strong>[29969-57-1]2-chloro-6-nitro-quinoline</strong> (1.6 g, 7.67 mmol) in N-methyl-2-pyrrolidinone (15 ml) with the above described rac-6-fluoro-2,3-dihydro-benzofuran-3-ylamine (1.3 g, 8.43 mmol) and N-ethyldiisopropylamine (1.96 ml, 11.5 mmol) was stirred at 140 C. for 2 h. Cooled to room temperature, poured onto water and extracted twice with Ethyl acetate, dried over sodium sulfate and evaporated totally to give a crude product which was purified by silica gel column chromatography with heptane/dichloromethane followed by trituration with diethyl ether to give the title compound as a yellow solid (1.0 g, 40%); MS (ISP) m/e=326.2 (M+H+).
With hydrogen;nickel; In tetrahydrofuran; methanol; at 50.0℃; under 75007.5 Torr; for 18.0h;
Step B: rac-6-Fluoro-2,3-dihydro-benzofuran-3-ylamine A mixture of the above described 6-fluoro-benzofuran-3-one oxime (5.38 g, 32 mmol; HPLC 1.489 min) and Raney-Nickel (2.4 g) in tetrahydrofuran (125 mL) and methanol (125 mL) was hydrogenated at 100 bar hydrogen-pressure at 50 C. for 18 h. Filtered the catalyst off, washed with methanol and tetrahydrofuran, all volatiles very removed in vacuum to give the crude product which was purified by Si-NH2 column chromatography with n-heptane/ethyl acetate to give the title compound as a light brown liquid (1.65 g, 34%, HPLC 0.367 min 100%), MS (ISP) m/e=154.0 [(M+H)+].
34%
With hydrogen;Raney-Nickel; In tetrahydrofuran; methanol; at 50.0℃; under 75007.5 Torr; for 18.0h;
Step B: rac-6-Fluoro-2,3-dihydro-benzofuran-3-ylamine A mixture of the above described 6-fluoro-benzofuran-3-one oxime (5.38 g, 32 mmol; HPLC 1.489 min) and Raney-Nickel (2.4 g) in tetrahydrofuran (125 mL) and methanol (125 mL) was hydrogenated at 100 bar hydrogen-pressure at 50 C. for 18 h. Filtered the catalyst off, washed with methanol and tetrahydrofuran, all volatiles very removed in vacuum to give the crude product which was purified by Si-NH2 column chromatography with n-heptane/ethyl acetate to give the title compound as a light brown liquid (1.65 g, 34%, HPLC 0.367 min 100%), MS (ISP) m/e=154.0 [(M+H)+].
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