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Stage #1: With tert.-butyl lithium In tetrahydrofuran; pentane at -10 - 5℃; for 2 h; Stage #2: at -50 - 0℃; for 3 h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; pentane at 0℃; for 0.5 h;
3-methoxy-2-formylphenylboronic acid. A solution of t-butyl lithium (9.0 mL, 1.7 M in pentane) was added to a stirred solution of 2-(2-methoxyphenyl)-1,3-dimethylimidazolidine (2.0 g, 9.8 mmol) in THF (5 mL) at -10° C. under N2 and stirred at 0-5° C. for 2 hours. The reaction mixture was cooled to -50° C. and triisopropylborate (3.5 mL, 15 mmol) was added. The solution was slowly warmed to 0° C. in 3 hrs. HCl (120 mL of 2N) was added at 0° C. and let it stirred for 30 min. The mixture was warmed to room temperature and was diluted with ethyl acetate. The organic layer was washed ( 2.x. HCl (1 N), brine), dried ( sodium sulfate) and concentrated to afford yellow crude product which purified by reverse phase HPLC chromatography. Upon removal of solvent 3-methoxy-2-formylphenylboronic acid crystallized as a light yellow solid, 1.3 g (yield 75percent). ESI-MS m/e 177 (MH+).
3-methoxy-2-formylphenylboronic acid. A solution of t-butyl lithium (9.0 mL, 1.7 M in pentane) was added to a stirred solution of 2-(2-methoxyphenyl)-1,3-dimethylimidazolidine (2.0 g, 9.8 mmol) in THF (5 mL) at -10° C. under N2 and stirred at 0-5° C. for 2 hours. The reaction mixture was cooled to -50° C. and triisopropylborate (3.5 mL, 15 mmol) was added. The solution was slowly warmed to 0° C. in 3 hrs. HCl (120 mL of 2N) was added at 0° C. and let it stirred for 30 min. The mixture was warmed to room temperature and was diluted with ethyl acetate. The organic layer was washed ( 2.x. HCl (1 N), brine), dried ( sodium sulfate) and concentrated to afford yellow crude product which purified by reverse phase HPLC chromatography. Upon removal of solvent 3-methoxy-2-formylphenylboronic acid crystallized as a light yellow solid, 1.3 g (yield 75percent). ESI-MS m/e 177 (MH+).
With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃;
Methyl 11-cyclohexyl-6-hydroxy-7-methoxy-6H-isoindolo[2,1,-a]indole-3-carboxylate. A stirred mixture of methyl 2-Bromo-3-cyclohexyl- 1H-indole-6-carboxylate (1.27 g, 7.0 mmol), 3-methoxy-2-formylphenylboronic acid (2.37 g, 7.0 mmol), LiCl (1.18 g, 28 mmol) and Pd(PPh3)4 (200 mg, 0.17 mmol) in 1M Na2CO3 (25 mL, 25 mmol) and 1:1 ethaol-toluene (100 mL). The reaction mixture was heated under nitrogen at 80° C. for overnight. The reaction mixture was then diluted with ethyl acetate and water, and then acidified with an excess of dilute HCl (1N). The ethyl acetate layer was then collected and washed with water, brine and then dried (NaSO4). Evaporation of solvents afforded crude product which was triturated with DCM and hexanes to provide the title compound as a white solid, (1.9 g, 68percent yield). LC-MS: m/e 390 (M-H)-; 374( M-H)+.
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