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tert-butyl 4-(4-(4-((1-(tert-butyl)-4-oxo-1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl)methyl)-3-methylphenyl)pyridin-3-yl)piperazine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 3 steps
1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / 90 °C / Inert atmosphere
3: potassium carbonate; [1,1′-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere
5-(4-bromo-2-methylbenzyl)-1-(tert-butyl)-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
20%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h;
72.1 1. Synthesis of 5-(4-bromo-2-methylbenzyl)-1-(tert-butyl)-1,5,6,7-tetrahydro-4H- pyrazolo[4,3-c]pyridin-4-one
To a solution of 1-(tert-butyl)-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one (440 mg, 2.28 mmol) in THF (20 mL) was added sodium hydride (455 mg, 11.4 mmol, 60% purity) at 0 °C. The mixture was stirred at 20 °C for 30 minutes. Then 4-bromo-1-(chloromethyl)-2- methylbenzene (500 mg, 2.28 mmol) was added, and the mixture was stirred at 20 °C for 10 hours. The mixture was quenched with MeOH (2 mL) and concentrated under vacuum to give crude residue. The residue was purified by prep-TLC (ethyl acetate) to give 5-(4-bromo-2- methylbenzyl)-1-(tert-butyl)-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one as a white solid (170 mg, 20% yield). LCMS: m/z = M+H+: 375.9, 377.9.
20%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h;
72.1 1. Synthesis of 5-(4-bromo-2-methylbenzyl)-1-(tert-butyl)-1,5,6,7-tetrahydro-4H- pyrazolo[4,3-c]pyridin-4-one
To a solution of 1-(tert-butyl)-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one (440 mg, 2.28 mmol) in THF (20 mL) was added sodium hydride (455 mg, 11.4 mmol, 60% purity) at 0 °C. The mixture was stirred at 20 °C for 30 minutes. Then 4-bromo-1-(chloromethyl)-2- methylbenzene (500 mg, 2.28 mmol) was added, and the mixture was stirred at 20 °C for 10 hours. The mixture was quenched with MeOH (2 mL) and concentrated under vacuum to give crude residue. The residue was purified by prep-TLC (ethyl acetate) to give 5-(4-bromo-2- methylbenzyl)-1-(tert-butyl)-1,5,6,7-tetrahydro-4H-pyrazolo[4,3-c]pyridin-4-one as a white solid (170 mg, 20% yield). LCMS: m/z = M+H+: 375.9, 377.9.
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