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[ CAS No. 1536648-98-2 ]

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Chemical Structure| 1536648-98-2
Chemical Structure| 1536648-98-2
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Product Details of [ 1536648-98-2 ]

CAS No. :1536648-98-2 MDL No. :N/A
Formula : C12H12BrN3O2 Boiling Point : 411.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :310.15 g/mol Pubchem ID :83401196
Synonyms :

Safety of [ 1536648-98-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
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Application In Synthesis of [ 1536648-98-2 ]

  • Downstream synthetic route of [ 1536648-98-2 ]

[ 1536648-98-2 ] Synthesis Path-Downstream   1~5

  • 1
  • ethyl 1-(6-bromopyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylate [ No CAS ]
  • [ 125114-77-4 ]
  • ethyl 5-methyl-1-(6-(3-oxo-2,3-dihydro-1H-inden-4-yl)pyridin-2-yl)-1H-pyrazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a mixture of Intermediate 1 -3 (1 .03 g, 3.31 mmol), bis(pinacolato)diboron (0.84 g, 3.31 mmol), KOAc (0.65 g, 6.61 mmol) in dioxane (1 1 mL) was added chloro(2- dicyclohexylphosphino-2',6'-dimethoxy-1 ,1 '-biphenyl)[2-(2-aminoethylphenyl)]palladium(ll) - methyl-t-butyl ether adduct (CAS 1028206-58-7; 0.1 1 g, 0.165 mmol). The mixture was then stirred at 120 C under the microwave irradiation for 45 minutes. To the mixture was then added a solution of 7-bromo-2,3-dihydro-1 H-inden-1 -one (0.66 g, 3.14 mmol) in dioxane (1 1 mL), followed by sodium carbonate (1 M in water; 8.3 mL, 8.27 mmol) and Pd(dppf)CI2,CH2Cl2 adduct (CAS 95464-05-4; 0.14 g, 0.165 mmol). The whole mixture was then stirred under microwave irradiation for 30 min at 1 10 C. Celite was added to the reaction mixture and the mixture was concentrated. The residue was purified by flash column chromatography (0-50% EtOAc/heptane) to yield the title compound. MS (ESI+) m/z 362.3 (M+H).
  • 2
  • [ 1536648-98-2 ]
  • [ 1852497-36-9 ]
  • [ 1852495-50-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl 1-(6-bromopyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylate With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 20 - 90℃; for 2.5h; Stage #2: (4-(4-((4-bromo-2,3-dihydrobenzofuran-3-yl)amino)-3-methylphenyl)piperidin-1-yl)(cyclopropyl)methanone With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate In 1,4-dioxane; ethanol; water at 20 - 90℃; for 0.25h; 34.34.A.a Example 34-A. a). (±)-Ethyl 1 -(6-(3-((4-(1 -(cyclopropanecarbonyl)piperidin-4-yl)-2- methylphenyl)amino)-2,3-dihydrobenzofuran-4-yl)pyridin-2-yl)-5-methyl-1 H-pyrazole-4- carboxylate To a solution of ethyl 1 -(6-bromopyridin-2-yl)-5-methyl-1 H-pyrazole-4-carboxylate (Intermediate 1 -3) (155 mg, 0.50 mmol), bis(pinacolato)diboron (127 mg, 0.50 mmol), KOAc (82 mg, 0.83 mmol) in dioxane (1 .1 ml) at room temperature was added Pd(dppf)CI2,CH2Cl2 adduct (24 mg, 0.029 mmol). The mixture was then stirred at 90 °C for 2.5 h, and then cooled to room temperature. Separately, palladium diacetate (4.7 mg, 0.021 mmol) and 1 ,1 -bis(di-fe/f- butylphosphino)ferrocene (CAS 84680-95-5) (9.9 mg, 0.021 mmol) were stirred in EtOH (0.56 ml_) at 50 °C for 1 h, which was then added to the reaction mixture above. To this mixture was then added a solution of (±)-(4-(4-((4-bromo-2,3-dihydrobenzofuran-3-yl)amino)-3- methylphenyl)piperidin-1 -yl)(cyclopropyl)methanone (Intermediate 3-9) (190 mg, 0.42 mmol) in dioxane (1 .1 ml), followed by potassium phosphate (2M in water) (0.63 ml_, 1 .25 mmol). The mixture was then stirred at 90 °C for 0.25 h, and then cooled to room temperature. The aqueous phase was removed and the organic phase was concentrated. The resulting residue was purified by silica gel flash chromatography to afford the title compound. MS (ESI+) m/z 606.5 (M+H).
  • 3
  • [ 1536648-98-2 ]
  • [ 1852497-38-1 ]
  • [ 1852498-09-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl 1-(6-bromopyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylate With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 20 - 100℃; for 3h; Stage #2: tert-butyl 4-(4-((4-bromo-2,3-dihydrobenzofuran-3-yl)amino)-3-methylphenyl)piperidine-1-carboxylate With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 20 - 100℃; for 2h; 35.35.A Example 35-A. (±)-ferf-Butyl 4-(4-((4-(6-(4-(ethoxycarbonyl)-5-methyl-1 H-pyrazol-1 - yl)pyridin-2-yl)-2,3-dihydrobenzofuran-3-yl)amino)-3-methylphenyl)piperidine-1 - carboxylate To a solution of ethyl 1 -(6-bromopyridin-2-yl)-5-methyl-1 H-pyrazole-4-carboxylate (Intermediate 1 -3) (0.82 g, 2.65 mmol), bis(pinacolato)diboron (0.74 g, 2.92 mmol), KOAc (0.39 g, 3.98 mmol) in dioxane (20 ml) at room temperature was added P Pd(dppf)Cl2,CH2Cl2 adduct (0.13 g, 0.16 mmol). The mixture was then stirred at 100 °C for 3 h, and then cooled to room temperature. To the reaction mixture were then added a solution of (±)-fe/?-butyl 4-(4-((4- bromo-2,3-dihydrobenzofuran-3-yl)amino)-3-methylphenyl)piperidine-1 -carboxylate (Intermediate 3-11) (0.9 g, 1 .86 mmol) in dioxane / H20 (15 mL/15 mL), K3P04 (1 .69 g, 7.96 mmol), and Pd(dppf)Cl2,CH2Cl2 adduct (0.22 g, 0.27 mmol). The mixture was then stirred at 100 °C for 2 h, and then cooled to room temperature. The reaction mixture was then diluted with EtOAc, and then washed successively with H20 and brine, dried over Na2S04, filtered, and then concentrated. The resulting residue was purified by flash chromatography (0% to 25% EtOAc in hexanes) to afford the title compound. MS (ESI+) /z 638.4 (M+H).
  • 4
  • [ 1536648-98-2 ]
  • [ 1852497-66-5 ]
  • [ 1852498-11-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl 1-(6-bromopyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylate With chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl] palladium(II) methyl-tert-butylether; potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 110℃; for 3h; Stage #2: 3-(4-(1-(cyclopropanecarbonyl)piperidin-4-yl)-2-methylbenzyl)-2,3-dihydro-1H-inden-4-yl trifluoromethanesulfonate With potassium phosphate; chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl] palladium(II) methyl-tert-butylether In 1,4-dioxane; water at 20 - 100℃; for 15h; 37.27.A.a Example 37-A. a.) (±)-Ethyl 1 -(6-(3-(4-(1 -(cyclopropanecarbonyl)piperidin-4-yl)-2- methylbenzyl)-2,3-dihydro-1 H-inden-4-yl)pyridin-2-yl)-5-methyl-1 H-pyrazole-4-carboxylate To a solution of Intermediate 1 -3 (137 mg, 0.44 mmol), bis(pinacolato)diboron (1 12 mg, 0.44 mmol), and KOAc (80 mg, 0.80 mmol) in dioxane (2.0 ml_) was added chloro(2- dicyclohexylphosphino-2',6'-dimethoxy-1 ,1 '-biphenyl)[2-(2-aminoethylphenyl)]palladium(ll)- methyl-f-butyl ether adduct (CAS 1028206-58-7; 13.5 mg, 0.020 mmol). The mixture was stirred at 1 10 °C for 3 h, and then cooled to room temperature. To a solution of (±)-3-(4-(1 -(cyclopropanecarbonyl)piperidin-4-yl)-2-methylbenzyl)-2,3-dihydro- 1 H-inden-4-yl trifluoromethanesulfonate (Intermediate 6-1) (209 mg, 0.40 mmol) in dioxane (2.0 ml_) was added the reaction mixture above, followed by 2M aq. K3P04 (0.4 ml_, 0.80 mmol) and chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1 ,1 '-biphenyl)[2-(2- aminoethylphenyl)]palladium(ll)-methyl-f-butyl ether adduct (CAS 1028206-58-7; 13.5 mg, 0.020 mmol). The mixture was then stirred at 100 °C for 15 h, and then cooled to room temperature, and then concentrated with Celite. The resulting residue was purified by silica gel flash chromatography to afford the title compound. MS (ESI+) m/z 603.5 (M+H).
  • 5
  • [ 134653-70-6 ]
  • [ 26944-71-8 ]
  • ethyl 1-(6-bromopyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 70℃; for 1.5h; A mixture of <strong>[26944-71-8]2-bromo-6-hydrazinylpyridine</strong> (5.04 g, 26.8 mmol) and ethyl 2-acetyl-3- (dimethylamino)acrylate (CAS 51 145-57-4; 4.96 g, 26.8 mmol) in EtOH (81 ml) was heated to 70 C for 1 .5 h. The reaction mixture was then allowed to cool to room temperature and a precipitate formed. Water (80 ml_) was then added to the mixture and the resulting heterogeneous mixture was filtered. The filter cake was washed with water and dried under reduced pressure to yield the title compound. MS (ESI+) m/z 310.1 (M+H).
In ethanol; at 70℃; for 1.5h;Inert atmosphere; A mixture of <strong>[26944-71-8]2-bromo-6-hydrazinylpyridine</strong> (5.04 g, 26.8 mmol) and ethyl 2-acetyl-3- (dimethylamino)acrylate (CAS 51 145-57-4; 4.96 g, 26.8 mmol) in EtOH (81 mL) was heated to 70 C for 1 .5 h. The reaction mixture was then allowed to cool to room temperature during which time a precipitate formed. Water (80 mL) was then added to the mixture and the resulting heterogeneous mixture was filtered. The filter cake was washed with water and dried under reduced pressure to yield the title compound. MS (ESI+) m/z 310.1 (M+H).
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