ChemicalBook CAS DataBase List 4-BOC-1-(5-BROMO-2-PYRIDYL)PIPERAZINE

4-BOC-1-(5-BROMO-2-PYRIDYL)PIPERAZINE synthesis

8synthesis methods

Product Name:4-BOC-1-(5-BROMO-2-PYRIDYL)PIPERAZINE
CAS Number:153747-97-8
Molecular formula:C14H20BrN3O2
Molecular Weight:342.23

53939-30-3 Synthesis

53939-30-3
465 suppliers
$5.00/1g

57260-71-6 Synthesis

57260-71-6
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$5.00/5g

153747-97-8
94 suppliers
$7.00/250mg

Yield: 81.5%

Reaction Conditions:

with potassium carbonate in acetonitrile at 110; for 12 h;

Steps:

17.1 Step 1’) Synthesis of tert-butyl 4-(5 -bromopyridin-2-yl)piperazine- 1 -carboxylate
General procedure: To 1,4-dioxane (30 mL) were added tert-butyl piperazine-1-carboxylate (2.89 g, 15.51 mmol), 5-bromo-2-chloropyrimidine (2.00 g, 10.34 mmol) and potassium carbonate (2.86 g, 20.68 mmol) sequentially. The mixture was heated to 110 °C, after stirring for 12 hours, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (3.15 g, 88.7%).; The title compound was prepared using tert-butyl piperazine-1-carboxylate (1.45 g, 7.79 mmol),5-bromo-2-chloropyridine (1.00 g, 5.20 mmol) and potassium carbonate (1.44 g, 10.39 mmol) in acetonitrile (30 mL) according to the process described in Step 4 of Example 1, and the crude product was purified by silica gel chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as a pale yellow solid (1.45 g, 8 1.5%).MS (ESI, pos. ion) m/z: 342.1 [M+H] and‘H NMR (600 MHz, CDC13): (ppm) 8.17 (d, J 2.4 Hz, 1H), 7.52 (dd, J 9.0, 2.5 Hz, 1H), 6.52 (d, J 9.0 Hz, 1H), 3.55 - 3.49 (m, 4H), 3.49 - 3.45 (m, 4H), 1.46 (s, 9H).

References:

SUNSHINE LAKE PHARMA CO., LTD.;ZHANG, Yingjun;JIN, Chuanfei;LIANG, Haiping;YI, Chao;ZHANG, Ji WO2016/192657, 2016, A1 Location in patent:Page/Page column 65

624-28-2 Synthesis