ChemicalBook CAS DataBase List S)-1-(sec-butyl)-N-((4,6-diMethyl-2-oxo-1,2-dihydropyridin-3-yl)Methyl)-3-Methyl-6-(6-(piperazin-1-yl)pyridin-3-yl)-1H-indole-4-carboxaMide

S)-1-(sec-butyl)-N-((4,6-diMethyl-2-oxo-1,2-dihydropyridin-3-yl)Methyl)-3-Methyl-6-(6-(piperazin-1-yl)pyridin-3-yl)-1H-indole-4-carboxaMide synthesis

9synthesis methods

Product Name:S)-1-(sec-butyl)-N-((4,6-diMethyl-2-oxo-1,2-dihydropyridin-3-yl)Methyl)-3-Methyl-6-(6-(piperazin-1-yl)pyridin-3-yl)-1H-indole-4-carboxaMide
CAS Number:1346574-57-9
Molecular formula:C31H38N6O2
Molecular Weight:526.67

1-(5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDIN-2-YL)PIPERAZINE

871125-86-9

1H-Indole-4-carboxaMide, 6-broMo-N-[(1,2-dihydro-4,6-diMethyl-2-oxo-3-pyridinyl)Methyl]-3-Methyl-1-[(1S)-1-Methylpropyl]-

1346574-54-6

S)-1-(sec-butyl)-N-((4,6-diMethyl-2-oxo-1,2-dihydropyridin-3-yl)Methyl)-3-Methyl-6-(6-(piperazin-1-yl)pyridin-3-yl)-1H-indole-4-carboxaMide

1346574-57-9

Synthesis of (S)-6-bromo-1-(sec-butyl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-methyl-1H-indole-4-carboxamide from 2-(piperazin-1-yl)pyridine-5-boronic acid pinacol ester and (S)-6-bromo-1-(sec-butyl)-N-((4,6-dimethyl-2-oxo-1,2- dihydropyridin-3-yl)methyl)-3-methyl-6-(6-(piperazin-1-yl)pyridin-3-yl)-1H-indole-4-carboxamide was prepared in the following general procedure: in a 100 mL three-necked flask (S)-6-bromo-1-(sec-butyl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-methyl-1H-indole-4-carboxamide was added. indole-4-carboxamide (365 mg, 0.82 mmol), pinacol ester of 2-(piperazin-1-yl)pyridine-5-boronic acid (309 mg, 1.07 mmol, 1.3 eq.), potassium phosphate (522 mg, 2.46 mmol, 3 eq.), water, and 1,4-dioxane solvent. Subsequently, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (53.9 mg, 0.066 mmol) was added under nitrogen protection and the reaction mixture was heated to 90 °C for the reaction. Upon completion of the reaction, the target product was purified to give 400 mg in 92% yield.

871125-86-9
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1346574-54-6 Synthesis

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1346574-57-9
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Yield:1346574-57-9 92%

Reaction Conditions:

with palladium bis[bis(diphenylphosphino)ferrocene] dichloride in water at 90;Inert atmosphere;Reagent/catalyst;

Steps:

79 synthesis of (S)-6-bromo-1-(isobutyl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-methyl-6-(6-(p-dinitrogenhexane-2-yl)piperidin-2-yl)-1-H-indole-4-carboxamide
add (S) -6- bromo-1- (isobutyl) in 100mL three-necked flask - N - ((4,6Dimethyl-2-oxo-1,2-dihydropyridin-3-yl) methyl) -3-methyl-1 Hydrogen - indole carboxamide (365mg,0.82mmol), 2- (piperazin-1-yl) pyridine-5-boronic acid pinacol ester (309mg, 1.07mmol, 1.3eq), phosphoric acidPotassium (522mg, 2.46mmol, 3eq), water and 1,4-epoxy hexadecane solvent. Then, under a nitrogen blanketWas added [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) dichloromethane complex (53.9mg,0.066 mmol), and reaction at 90 deg.] C, after purification to give the desired product 400mg (92% yield

References:

Changzhou University;Chen, Xin;Lu, Chen CN105541801, 2016, A Location in patent:Paragraph 0118

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