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With N-Bromosuccinimide; In dichloromethane; at 0 - 20℃; for 16.0h;
A solution of crude 7-chloropyrazolo[1,5-a]pyrimidine (44.2 g, 289 mmol) in dichloromethane (289 mL) was cooled to 0 0C using an ice bath. Lambda/-bromosuccinimide(51.4 g, 289 mmol) was added slowly to the solution that was stirred for 16 h at room temperature. The dark orange solution was diluted with dichloromethane (200 mL) and was washed with 10% potassium carbonate solution (3 x 150 mL) and brine (100 mL).The organic phase was dried and concentrated to give a dark orange solid, which was triturated using MeOH to yield the desired product, 3-bromo-7-chloropyrazolo[1,5- EPO <DP n="46"/>a]pyrimidine (50.9 g, 76%) as a yellow solid. HPLC 96%; lH NMR (250 MHz, CDCI3) delta 8.49 (d, J = 5.2 Hz, 1H), 8.25 (s, 1H), 7.07 (d, J = 5.2 Hz, 1H); 13C NMR (62.9 MHz, DMSO) delta 150.4, 145.9, 144.7, 138.5, 109.5, 84.7.
7-(6-fluoro-5-methylpyridin-3-yl)pyrazolo[1,5-a]pyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
51%
With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl?)]palladium(II); caesium carbonate; In 1,4-dioxane; water; at 85℃; for 2.0h;Inert atmosphere;
A stirred solution of 7-chloropyrazolo[1,5-ajpyrimidine (50 mg, 0.326mmol), <strong>[904326-92-7](6-fluoro-5-methylpyridin-3-yl)boronic acid</strong> (50.4 mg, 0.326 mmol), andcesium carbonate (212 mg, 0.65 1 mmol) in a mixture of 1,4-dioxane (5 mL) andwater (0.5 mL) was purged with nitrogen. XPhos generation precatalyst (38.4mg, 0.049 mmol) was added in one portion and the reaction mixture was heated to 85C and stirred for 2 h. The solution was concentrated under reduced pressure. Water(50 mL) was added and the solution was extracted with EtOAc (2 x 50 mL). Thecombined organic extracts were washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc in hexanes) to afford 7-(6-fluoro- 5-methylpyridin-3-yl)pyrazolo[ 1 ,5-ajpyrimidine (38 mg, 0.165 mmol, 51% yield).LCMS (ESI) m/e 229.2 [(M+H), calcd for C12H10FN4, 229.11; LC/MS retentiontime (method D) tR = 1.86 mm.
7-(5-chloro-6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
19%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 85℃; for 2.0h;Inert atmosphere;
A stirred solution of 7-chloropyrazolo[1,5-ajpyrimidine (100 mg, 0.651 mmol), <strong>[1366482-32-7](5-chloro-6-fluoropyridin-3-yl)boronic acid</strong> (114 mg, 0.65 1 mmol), and cesium carbonate (424 mg, 1.302 mmol) in a mixture of 1,4-dioxane (5 mL) and water (0.5 mL) was purged with nitrogen. PdC12(dppf)-CH2C12 adduct (80 mg, 0.098mmol) was added in one portion and the reaction mixture was heated to 85 C and stirred for 2 h. The solution cooled to room temperature and was concentrated under reduced pressure. Water (50 mL) was added and the solution was extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with water (50mL) and brine (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc in hexanes) to afford 7-(5-chloro-6-fluoropyridin-3-yl)pyrazolo[ 1,5 -alpyrimidine (56 mg, 0.122 mmol, 19 % yield). LCMS (ESI) m/e 249.0 [(M+H), calcd for C11H7C1FN4, 249.01; LC/MS retention time (method B) tR = 0.95 mm.
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