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7-chloro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
In tetrahydrofuran; at 60℃;Sealed tube;
<strong>[24484-98-8]2,3-diamino-4-chloropyridine</strong> (6.97 mmol; 1000.00 mg) was combined with 1,1'carbonyldiimidazole(7 .03 mmol; 1140.00 mg) into THF (370.29 mmol; 30.00 ml) . The mixturewas then heated to 60C over night in a sealed tube. A white precipitate formed. The reactionwas cooled toRT. The solids were removed via filtration and washed with 5 mL of THF. Thesolids were then dried on the pump to give 7-Chloro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one(1007.2 mg; 84%) MS: m/z = 170 [M+H]+
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 140℃; for 2h; Sealed tube; Inert atmosphere; Microwave irradiation;
2 7 -( 4-Aminomethyl-3-fluoro-phenyl)-1,3-dihydro-imidazo[ 4,5-b ]pyridin-2-one (Step 2)
To a 5 mL microwave vial was added, 4-(aminomethyl)-3-fluorophenylboronic acid,hcl (0.00 mol; 1.20 eq.; 363.43 mg), Pd(dppf)*DCM (0.00 mol; 0.10 eq.; 120.40 mg), andPotassium Carbonate (0.00 mol; 3.00 eq.; 611.26 mg). The vial was sealed and evacuated/backfilled with nitrogen 3 times. Next was added dioxane (5.00 ml) and water (0.50 ml). The vial wasevacuated/back filled with nitrogen 3 times. The reaction stirred at 140°C in the microwave for 2hours. The reaction was partially concentrated and diluted with 4 ml DMSO. The reactionmixture was filtered and purified via prep HPLC with 0.1% NH40H modified mobile phaseusing a gradient of 5-40% CH3CN/Water to give 7-(4-Aminomethyl-3-fluoro-phenyl)-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (117.00 mg; 30%). MS: m/z = 259 [M+H]+
With dipotassium hydrogenphosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 130℃; for 1h; Sealed tube; Inert atmosphere; Microwave irradiation;
18 3-tert-Butyl-[1,2,4]oxadiazole-5-carboxylic acid 3-hydroxymethyl-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b ]pyridin-7-yl)-benzylamide Step 2.
To a 10 mL reaction tube was added 7-Chloro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (0.20 mmol; 1.00 eq.; 35.00 mg), 3-tert-Butyl-[1,2,4]oxadiazole-5-carboxylic acid (1-hydroxy-1 ,3-dihydro-benzo[ c ][ 1 ,2]oxaborol-5-ylmethyl)-amide (0.25 mmol; 1.29 eq.; 80.00mg), and 1,1 '-bis( diphenylphosphino )ferrocene-palladium(ii)dichloride dichloromethanecomplex (0.02 mmol; 0.10 eq.; 16.01 mg). The tube was sealed and flushed with Ar. To thereaction mixture was added potassium phosphate, dibasic (0.39 mmol; 2.00 eq.; 443.16 mg; 0.39ml), Sodium acetate (0.39 mmol; 2.00 eq.; 0.39 ml), and MeCN (47.86 mmol; 244.10 eq.;1965.00 mg; 2.50 ml) via syringe. The reaction tube was degassed with argon and heated to 130°C for 1h in microwave. Reaction was purified directly via column chromatography using agradient of 2-10% MeOH/DCM on 15 g silica. The material was then dissolved in DMSO andpurified via reverse phase preparative chromatography with 0.1% NH40H modified mobilephases using a gradient of 5-95% CH3CN/H20 over 15 minutes, to afford the title compound(1.60 mg; 1.9%). MS: m/z = 423 [M+H]+. HPLC Purity= 98%.
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