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To Imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (1 eq, 33 mmol, 5.8 g) in acetic acid (60 ml) under an inert atmosphere of argon is added dropwise bromine (1 eq, 33 mmol, 1.7 ml). After stirring at room temperature for 1 hour, the reaction mixture is filtered to afford the title compound as a beige solid; [M+H]+ =255/257
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 95℃; for 16.0h;
To a solution of 3-Bromo-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (leq, 23 mmol, 5.9 g), 2-chloropyrid-4-yl boronic acid (1.05 eq, 24 mmol, 3.8 g), Na2COs (2 eq, 46 mmol, 4.9 g) in dioxane (40 ml) and water (15 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (0.1 eq, 2.4 mmol, 1.6 g). The reaction mixture is heated at 95 C for 16 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions <n="124"/>are washed with brine, dried (MgStheta4) and concentrated in vacuo. The residue is purified by chromatography on silica eluting with 0-10% MeOH in EtOAc to afford the title compound; [M+H]+ = 287/289.
N-cyclopropyl-2-fluoro-4-methyl-5-(1H-pyrazol-4-yl)benzamide[ No CAS ]
methyl 3-{4-[5-(cyclopropylcarbamoyl)-4-fluoro-2-methylphenyl]-1H-pyrazol-1-yl}imidazo[1,2-a]pyridine-6-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
374 mg
With potassium phosphate; copper(l) iodide; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; In N,N-dimethyl-formamide; at 20 - 60℃; for 22.0h;Inert atmosphere;
A mixture of <strong>[886361-98-4]3-bromo-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester</strong> (492 mg, 1.93 mmol), I-37 (500 mg, 1.93 mmol), potassium phosphate (819 mg, 3.86 mmol), trans-N,N?-dimethyl-cyclohexane-1,2-diamine (0.2 ml, 1.54 mmol) in anhydrous DMF (8.0 ml) is degassed with nitrogen. To this mixture is added CuI (147 mg, 0.77 mmol). The reaction is placed under nitrogen and the reaction is heated at 60 C. for 4 h. The mixture is then cooled to room temperature and stirred for 18 h. The reaction is then diluted with water and extracted with EtOAc (3×). The organic layers are combined, washed with water, then brine, and dried over sodium sulfate. The solution is then filtered and concentrated under reduced pressure. The resulting residue is purified by flash silica gel chromatography to provide 374 mg of the title compound (2).
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