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4-methyl-1-(2-methyl-quinolin-4-yl)-1H-pyrrole-3-carboxylic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With caesium carbonate; In DMF (N,N-dimethyl-formamide); at 80℃; for 60h;
1 [MMOL.] (139 mg) [OF 4-METHYLPYRROLE-3-CARBOXYLIC] acid methyl ester, [1. 1 MMOL] (195 mg) 4-chloro-2-methyl-quinoline and 1.2 mmol (390 mg) of Cs2C03 are suspended in 3 ml of dry [DMF.] The mixture is stirred for 60h at [80 C] under Argon, allowed to cool to room temperature, and diluted with water (20 [ML).] Part of the product precipitates and is filtered off. The filtrate is extracted twice with ethyl acetate (20 ml portions). The combined extracts are dried over anhydrous Na2S04 and evaporated. The residue is combined with the precipitate and purified by prep. HPLC to yield 4-methyl-1- (2- [METHYL-QUINOLIN-4-YL)-1] H-pyrrole-3-carboxylic acid methyl ester (MS molpeak 281 [(M+H, ELECTROSPRAY IONISATION) ) AS AN OFF-WHITE FOAM AFTER FREEZE-DRYING.]
With toluene-4-sulfonamide; In toluene; at 120℃; for 12h;
General procedure: In a dried two-neck round-bottom flask, 4-chloro-2-methylquinoline (6a, 0.99 g, 4.2 mmol), PhCHO (668 mg,6.3 mmol) and p-toluene sulphonamide (2.06 g, 6.3 mmol)(Scheme 1) were taken. Dry toluene (21 mL) was added andthe magnetically stirred slurry was refluxed for 12 h. Reactionprogress was monitored by TLC. After completion, thereaction mixture was poured into water (25 mL) and thenextracted with ethyl acetate (25 mL). The organic layer waswashed with water (25 mL) twice, followed by brine (25 mL).The organic layer was dried over anhydrous sodium sulfateand concentrated in vacuo. The crude was purified via columnchromatography (5% ethyl acetate in hexane) to yieldcompound 7 as a yellow crystalline solid (1.04 g).
2-methyl-N-[3-(oxazol-5-yl)phenyl]quinolin-4-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91.15%
With indium(III) chloride; In acetonitrile; at 110 - 170℃;Microwave irradiation;
General procedure: To a solution of 3-aminobiphenyl derivatives with appropriate substituted group of 4-chloroquinoline in 10-15mL acetonitrile, and added indium (III) chloride as the catalyst in the Glass vial, followed by placing in the microwave reactor. Microwave wattage was between 300 and 900W, heating at 110C to 170C for 30min to 3h. After the completion of reaction, the mixture was concentrated under vacuum and then subjected to purify by flash chromatography with different proportion of dichloromethane/methanol. The solid was recrystallized in acetonitrile and filtered to obtained the desired compound.
91.15%
With indium(III) chloride; In acetonitrile; at 110 - 170℃;Microwave irradiation;
General procedure: To a solution of 3-aminobiphenyl derivatives with appropriate substituted group of 4-chloroquinoline in 10-15mL acetonitrile, and added indium (III) chloride as the catalyst in the Glass vial, followed by placing in the microwave reactor. Microwave wattage was between 300 and 900W, heating at 110C to 170C for 30min to 3h. After the completion of reaction, the mixture was concentrated under vacuum and then subjected to purify by flash chromatography with different proportion of dichloromethane/methanol. The solid was recrystallized in acetonitrile and filtered to obtained the desired compound.
Chemistry
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