ChemicalBook CAS DataBase List 2-ISOPROPYL PYRIDINE

2-ISOPROPYL PYRIDINE synthesis

14synthesis methods

Product Name:2-ISOPROPYL PYRIDINE
CAS Number:644-98-4
Molecular formula:C8H11N
Molecular Weight:121.18

109-04-6 Synthesis

109-04-6
530 suppliers
$6.00/25g

75-26-3
474 suppliers
$10.00/10g

644-98-4
97 suppliers
$6.00/100mg

Yield: 10%

Reaction Conditions:

with pyridine;tetrabutylammomium bromide;4,4'-di-tert-butyl-2,2'-bipyridine;magnesium chloride;nickel dibromide;zinc in N,N-dimethyl acetamide at 30;Schlenk technique;Inert atmosphere;Glovebox;

Steps:

General Procedure for alkylation of halogenated pyridines with secondary alkyl bromides
General procedure: To a flame-dried Schlenk tube equipped with a magnetic stir bar was loaded alkyl bromide (0.15 mmol, 100 mol%, solid), halogenated pyridine (0.30 mmol, 300 mol%, solid), ligand (0.015 mmol, 10 mol%), zinc powder (0.45 mmol, 300 mol%). The tube was capped with a rubber septum and moved to a dry glove box, at which NiBr2 (0.015 mmol, 10 mol%), MgCl2 (0.15 mmol, 100 mol%) and Bu4NBr (0.075 mmol, 50 mol%) were added. Then the tube was moved out of the glove box. Alkyl bromide (0.15 mmol, 100 mol%, liquid), halogenated pyridine (0.30 mmol, 300 mol%, liquid), pyridine (0.15 mmol, 100 mol%) and DMA(1.0 mL) were added via syringe. After the reaction mixture was allowed to stir overnight under N2 atmosphere at 30 °C, it was directly loaded onto a silica column without work-up. The residue in the reaction vessel was rinsed with small amount of DCM or eluent. Flash column chromatography provided the product as solid or oil.

References:

Liu, Huiyan;Liang, Zhuye;Qian, Qun;Lin, Kunhua [Synthetic Communications,2014,vol. 44,# 20,p. 2999 - 3007] Location in patent:supporting information

100-71-0 Synthesis