ChemicalBook CAS DataBase List 2,6-Di(1-pyrazolyl)pyridine

2,6-Di(1-pyrazolyl)pyridine synthesis

10synthesis methods

Product Name:2,6-Di(1-pyrazolyl)pyridine
CAS Number:123640-38-0
Molecular formula:C11H9N5
Molecular Weight:211.22

288-13-1
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626-05-1 Synthesis

626-05-1
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123640-38-0
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$43.00/100mg

Yield: 95%

Reaction Conditions:

Stage #1:NH-pyrazole with potassium tert-butylate in dimethyl sulfoxide at 0; for 0.166667 h;Inert atmosphere;Schlenk technique;
Stage #2:2,6-Dibromopyridine in dimethyl sulfoxide at 140; for 24 h;Inert atmosphere;Schlenk technique;

Steps:

2. Synthesis of Ligands
L_N5: An oven-dried vial was charged with pyrazole (1.36 g, 20 mmol), t-BuOK (2.24 g, 20 mmol) and the mixture was stirred for 10 min under 0 °C. Then,2,6-dichloropyridinewas added. The reaction mixture was stirred for 24 h at 140 °C. It was cooled to room temperature. Water (50 mL) was added and the product precipitated as solid. The solid was filtered, washed with water and extracted with dichloromethane. The organic layer was washed with water to remove DMSO. Purification by chromatography on silica gel (first elution with 0.4-1.0% CH₃OH in CH₂Cl₂to remove starting materials and byproducts, then elution with 0-0.4% CH₃OH in CH₂Cl₂) gave pure L_N5 (4.01 g, 95%). Its spectroscopic data is consistent with literature report.²¹H NMR (400 MHz, CDCl₃): δ 8.58-8.57 (m, 2H), 7.94-7.93 (m, 1H), 7.89-7.83 (m, 2H), 7.77 (d,J= 1.0 Hz, 2H), 6.53-6.48 (m, 2H). ¹³C NMR (101 MHz, CDCl₃) δ 150.07, 142.41, 141.45, 127.03, 109.40, 107.99.