ChemicalBook CAS DataBase List 1-METHYL-4-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORALAN-2-YL)PYRIDINE-2-YL]PIPERAZINE

1-METHYL-4-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORALAN-2-YL)PYRIDINE-2-YL]PIPERAZINE synthesis

6synthesis methods

Product Name:1-METHYL-4-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORALAN-2-YL)PYRIDINE-2-YL]PIPERAZINE
CAS Number:918524-63-7
Molecular formula:C16H26BN3O2
Molecular Weight:303.21

73183-34-3

5-Bromo-2-(4-Boc-piperazin-1-yl)pyridine

364794-58-1

1-METHYL-4-[5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABORALAN-2-YL)PYRIDINE-2-YL]PIPERAZINE

918524-63-7

Using 1-(5-bromopyridin-2-yl)-4-methylpiperazine (1.5 g, 5.9 mmol), bis(pinacolato)diboron (1.6 g, 6.5 mmol), potassium acetate (1.8 g, 18 mmol), and Pd(dppf)2Cl2[CH2Cl2] (0.73 g, 0.89 mmol) as raw materials, the mixture was dissolved under nitrogen protection in DMSO (20 mL) and the reaction was stirred at 80 °C overnight. After completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate (EA). The organic phases were combined and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, v/v=3 to pure ethyl acetate) to afford the target product, 6-(4-methyl-1-piperazinyl)pyridine-3-boronic acid pinacol ester (1.0 g, 56% yield) as a brown solid. Mass spectrometry (MS) analysis showed m/z 304 (M+H)+.

73183-34-3
590 suppliers
$6.00/5g

364794-58-1
93 suppliers
$25.00/250mg

918524-63-7
147 suppliers
$15.00/100mg

Yield:918524-63-7 56%

Reaction Conditions:

with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂;potassium acetate in dimethyl sulfoxide at 80;Inert atmosphere;

Steps:

A mixture of 15 (1.5 g, 5.9 mmol), bis(pinacolato)diboron (1.6 g, 6.5 mmol), potassium acetate(1.8 g, 18 mmol) and Pd(dppf)²Cl²[CH²Cl²] (0.73 g, 0.89 mmol) in DMSO (20 mL) was protected with nitrogen and stirred at 80 ^oC overnight. The mixture was diluted with water and extracted with EA. The organic solution was concentrated in vacuo and the residue was purified by silica gel column chromatography (PE/EA, v/v = 3 to EA) to give 1.0 g of 16 (56% yield) as a brown solid. MS: m/z 304 (M+H)⁺.

References:

DANA-FARBER CANCER INSTITUTE, INC.;BRADNER, James, E.;QI, Jun;WONG, Kwok, Kin WO2016/73956, 2016, A1 Location in patent:Paragraph 00361

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61676-62-8 Synthesis