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1-(isoquinol-1-yl)-3-methoxycarbonyl-4-methyl-1H-pyrrole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
0.208 g (6.5 [MMOL)] of sodium hydride, at 75% by weight in liquid petroleum jelly, is added at a temperature in the region of [20C] under an argon atmosphere to a solution of 0.903 g (6.5 [MMOL)] of [3-METHOXYCARBONYL-4-METHYL-1 H-PYRROLE] in 20 cm3 of [DIMETHYLFORMAMIDE.] After stirring at a temperature in the region [OF 40C] for 0.3 hour, 1. 07 g (6.5 [MMOL)] of 1-chloroisoquinoline and 10 cm3 of dimethylformamide are added. After stirring at a temperature in the region of [120C] for 4 hours, the reaction mixture is poured into 200 cm3 of salt water and then extracted with 100 cm3 of ethyl acetate. The organic phase is partially concentrated under reduced pressure. 100 cm3 of sa . t water are added to the residue, which is then extracted with 50 cm3 of ethyl acetate. The organic phase is dried over anhydrous magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2. 7 kPa) to give a solid which is purified by silica gel chromatography [eluent : cyclohexane/dichloromethane/ethyl acetate [(60/36/4] by volume)]. After concentrating the fractions under reduced pressure (2.7 kPa), 1.5 g of [1-(ISOQUINOL-1-YL)-3-METHOXYCARBONYL-4-METHYL-1 H-PYRROLE ARE] [OBTAINED. MASS SPECTRUM (EL) : M/E 266 (M+. ), M/E 235.]
3-methoxycarbonyl-1-(isoquinol-1-yl)-5-methyl-1H-indole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1.65 g (11.9 [MMOL)] of potassium carbonate are added at [25C] under an argon atmosphere to 0.900 g (4.75 [MMOL)] of [3-METHOXYCARBONYi-5-METHYL-1 H-INDOLE] in 10 cm3 of dimethyl sulphoxide. After stirring at [25C] for 0.5 hour, 0.677 cm3 (4.75 [MMOL)] of 1-chloroisoquinoline is added. After stirring at [100C] for 48 hours, the reaction mixture is cooled and diluted with 100 cm3 of ethyl acetate and then washed with 3 times 50 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.50 g of a residue which is purified by flash chromatography [eluent : cyclohexane/ethyl acetate (8/2 by volume)]. After concentrating the fractions to dryness under reduced pressure (2.7 kPa), [1. 4 G OF 3-METHOXYCARBONYL-1- (ISOQUINOL-1-YL)-5-METHYL-1 H-INDOLE] are obtained in the form of a white solid melting at [142C.]
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