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With potassium carbonate; In ethanol; at 140℃;Schlenk technique;
General procedure: A mixture of indole-3-carboxylic acid 1 (0.50 mmol) and K2CO3 (13.8 mg, 0.10 mmol, 20 mol%) in EtOH (3 mL) was added into a Schlenk flask (25 mL) and stirred at 140 C. The reaction was monitored by thin layer chromatography until the disappearance of starting material 1. Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography (petroleum ether/ethyl acetate 20:1 to 10:1).
(4-benzyl-4-hydroxy-1-piperidyl)-(2-methyl-1H-indol-3-yl)methanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃;
To a stirred solution of 0.1 g (0.57 mmol) <strong>[63176-44-3]2-methyl-1H-indole-3-carboxylic acid</strong> in 10 ml CH2Cl2 were added 0.14 g (0.73 mmol) EDC, 0.10 g (0.73 mmol) HOBt, 90 μl (0.63 mmol) Et3N and 0.11 g (0.57 mmol) 4-benzyl-piperidin-4-ol. The mixture was stirred overnight at RT and then poured onto water and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Flash chromatography (ethyl acetate) afforded 0.15 g (75%) of (4-benzyl-4-hydroxy-piperidin-1-yl)-(2-methyl-1H-indol-3-yl)-methanone as a white solid. ES-MS m/e (%): 349 (M+H+).
1-Benzyl-<strong>[63176-44-3]2-methyl-1H-indole-3-carboxylic acid</strong>; Using the procedure described in example 8 hereinafter, from <strong>[63176-44-3]2-methyl-1H-indole-3-carboxylic acid</strong> (described in J. Heterocyclic Chem. 1977, 14, 1123) was prepared 1-benzyl-<strong>[63176-44-3]2-methyl-1H-indole-3-carboxylic acid</strong>.
To a stirred solution of 0.50 g (3.1 mmol) <strong>[63176-44-3]2-methyl-1H-indole-3-carboxylic acid</strong> (described in J. Heterocyclic Chem. 1977, 14, 1123) in 5 ml DMF were added 0.27 g (6.75 mmol) of NaH (60% in oil). The mixture was stirred at RT for 30 min. and then 0.39 ml (3.28 mmol) of benzyl bromid were added. The mixture was stirred an additional hour and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Crystallization in Et2O afforded 0.61 g (78%) of 1-benzyl-<strong>[63176-44-3]2-methyl-1H-indole-3-carboxylic acid</strong> as a white solid.
With sodium hydride; In N,N-dimethyl-formamide; for 1.5h;
Acid Intermediates of Formula II Acid 1 1-Benzyl-<strong>[63176-44-3]2-methyl-1H-indole-3-carboxylic acid</strong> To a stirred solution of 0.50 g (3.10 mmol) <strong>[63176-44-3]2-methyl-1H-indole-3-carboxylic acid</strong> (described in J. Heterocyclic Chem. 1977, 14, 1123) in 5 ml DMF were added 0.27 g (6.75 mmol) of NaH (60% in oil). The mixture was stirred at room temperature for 30 min. and then 0.39 ml (3.28 mmol) of benzyl bromid were added. The mixture was stirred for one additional hour and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Crystallization from Et2O afforded 1-benzyl-<strong>[63176-44-3]2-methyl-1H-indole-3-carboxylic acid</strong>.
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