3-IODO-4-METHOXY-PYRIDINE synthesis
- Product Name:3-IODO-4-METHOXY-PYRIDINE
- CAS Number:89640-55-1
- Molecular formula:C6H6INO
- Molecular Weight:235.02
620-08-6
89640-55-1
The general procedure for the synthesis of 3-iodo-4-methoxypyridine from 4-methoxypyridine was as follows: n-butyllithium (ca. 1.6 M hexane solution, 1.5 mmol) was sequentially added to a stirred solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in tetrahydrofuran (THF, 2-3 mL) at 0 °C. After 5 min, n-butyllithium (ca. 1.6 M hexane solution, 1.5 mmol) was added. ZnCl2TMEDA complex (0.13 g, 0.50 mmol). The reaction mixture was continued to be stirred at 0 °C for 15 min and then 4-methoxypyridine (1.0 mmol) was added at 0-10 °C. After the reaction mixture was stirred for 2 h at room temperature, a THF (4 mL) solution of iodine (I2, 0.38 g, 1.5 mmol) was added. After the mixture was stirred overnight, the reaction was quenched by the addition of saturated aqueous sodium thiosulfate (Na2S2O3) solution (4 mL) and extracted with ethyl acetate (AcOEt, 320 mL). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. Finally, the target product, 3-iodo-4-methoxypyridine, was purified by silica gel column chromatography (eluent given in the product specification).
620-08-6
317 suppliers
$5.00/1g
89640-55-1
82 suppliers
$13.00/250mg
Yield: 89%
Reaction Conditions:
Stage #1:4-methoxypyridine with 2,2,6,6-tetramethyl-piperidine;n-butyllithium;zinc dichloro(N,N,N′,N′-tetramethylethylenediamine) in tetrahydrofuran;hexane at 20; for 2 h;Inert atmosphere;
Stage #2: with iodine in tetrahydrofuran;hexane at 20;Inert atmosphere;regioselective reaction;Concentration;
Steps:
4.2. General procedure 1
General procedure: To a stirred, cooled (0 C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2TMEDA[51] (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0 C before introduction of the substrate (1.0 mmol) at 0-10 C. After 2 h at room temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solutionof Na2S2O3 (4 mL) and extraction with AcOEt (320 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by chromatographyon silica gel (the eluent is given in the product description) led to the compounds described below.
References:
Hedidi, Madani;Bentabed-Ababsa, Ghenia;Derdour, Aïcha;Halauko, Yury S.;Ivashkevich, Oleg A.;Matulis, Vadim E.;Chevallier, Floris;Roisnel, Thierry;Dorcet, Vincent;Mongin, Florence [Tetrahedron,2016,vol. 72,# 17,p. 2196 - 2205]
67-56-1
782 suppliers
$7.29/5ml-f
89167-34-0
112 suppliers
$10.00/250mg
89640-55-1
82 suppliers
$13.00/250mg