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In water; at 150℃; for 12h;Sealed tube; Microwave irradiation;
General procedure: The aza-ellipticine analogs were produced using the following general reactionmethod. To a clean microwave safe reaction vial equipped with a stir bar was added theappropriate isatin analog (1.0 equiv., 0.2M in H20) and amino-picoline (3.0 equiv.). A concentrated acid like trifluoromethanesulfonic acid, or concentrated hydrochloric acid (0.2 equiv.) was then added. The vial was sealed and heated in a microwave at 150 C for 12 hours. The solvent was then removed using a rotary evaporator and the residuepurified on a Teledyne ISCO chromatography system using a Cl 8 reverse phase support(H20 with 0.1% Formic acid/MeCN gradient) to afford the desired aza-ellipticine analog. A summary of the compounds synthesized can be found in Table 2.The compound was synthesized as shown in Preparative Example B above. Purificationdone using a Teledyne ISCO Combiflash on a silica support using Dichloromethane:Acetonitrile (9:1). HPLC run on Agilent 1100 using water w/ 0.1% Formic acid:Acetonitrile 95:5 to 100% MeCN over a ten minute gradient on phenomenex 75x4.6mm C18 column. Rt: 4.8 minutes.1H-NMR (400 MHz, CD3OD) d 9.01 (s, 1H),8.87 (dd, IH), 8.45 (d, 1H), 8.30 (d, 1H), 7.77 (dd, 1H), 7.58 (m, 2H), 7.35 (dd, 1H). MSChemical Formula: C14H9N3, calculated mass, 219.08, observed 220.1 (M+1).
2-chloro-4-[(2-methyl-3-pyridyl)amino]pyridine-3-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With palladium diacetate; caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In 1,4-dioxane; at 50 - 150℃; for 0.583333h;Microwave irradiation; Sealed tube; Inert atmosphere;
To a 10-20 mL microwave vial were added sequentially <strong>[180995-12-4]2,4-dichloropyridine-3-carbonitrile</strong> (429 mg, 1.62 mmol), 2-methylpyridin-3-amine (175 mg, 1.62 mmol), palladium(II) acetate (7.3 mg, 0.032 mmol), bis(2-diphenylphosphinophenyl)ether (26 mg, 0.049 mmol), and CS2CO3(740 mg, 2.27 mmol). The vial was sealed and was evacuated and refilled with argon three times and dioxane (3.2 mL) was added. The vial was evacuated and refilled with argon once. The suspension was heated for 5 minutes in a 50 C oil bath under argon and then the sealed vial was heated for 30 minutes in a 150 C oil bath. The suspension was removed from the heating bath and stored at room temperature overnight. The crude reaction mixture was used directly in the next step
With palladium diacetate; caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In 1,4-dioxane;Sealed tube; Inert atmosphere; Heating;
To a 10-20 mL microwave vial were added sequentially 2, 4-dichloropyridine-3-carbonitrile (429 mg, 1.62 mmol) , 2-methylpyridin-3-amine (175 mg, 1.62 mmol) , palladium (II) acetate (7.3 mg, 0.032 mmol) , bis (2-diphenylphosphinophenyl) ether (26 mg, 0.049 mmol) , and Cs2CO3(740 mg, 2.27 mmol) . The vial was sealed and was evacuated and refilled with argon three times and dioxane (3.2 mL) was added. The vial was evacuated and refilled with argon once. The suspension was heated for 5 minutes in a 50 oil bath under argon and then the sealed vial was heated for 30 minutes in a 150 oil bath. The suspension was removed from the heating bath and stored at room temperature overnight. The crude reaction mixture was used directly in the next step.
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