3-Iodopyridine

light beige crystalline powder

Aromatic Finkelstein Reaction; General ProcedureThe reaction was carried out under argon using standard Schlenktechniques due to the moisture and oxygen sensitivity of the copper(I) iodide. A two-neck pear-shaped flask equipped with a refluxcondenser was charged with the (het)aryl bromide starting material, NaI (2 equiv per bromine to exchange), and CuI (5 molpercent per bromineto exchange). N, N′-Dimethylethylenediamine (L1) or N, N′-dimethyl-1, 2-cyclohexanediamine (L2) (10 molpercent per bromine toexchange) and anhydrous 1, 4-dioxane (0.5 mL per 1 mmol NaI)were added. The resulting suspension was heated to 110 °C for 18h. After cooling to r.t., the mixture was poured into aq 25percent NH3 solution.The blue solution was diluted to a doubled volume with H2Oand was extracted three times with CH2Cl2. In the case of the 2, 2′-bipyridines, the combined organic phases were additionally washedwith aq EDTA solution. Otherwise, the combined organic phaseswere solely washed with brine and dried with MgSO4. The solventwas removed under reduced pressure to give the desired product inpure form. If needed, the crude product can be purified by columnchromatography or recrystallization.General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBrGeneral procedure: A solution of iodopyridine 1-oxide 2a, 3a, or 7a (2 mmol) in CHGeneral procedure: To a 15 mL test tube with septum Cs2CO3 (0.6 mmol, 195 mg), aromaticcarboxylic acid (1) (0.3 mmol), [Ir(dF(CF3)ppy)2dtbbpy]PF6 (D) (6 μmmol, 6.7 mg), NIS (1.5mmol, 337.5 mg) and I2 (60 μmol, 20 molpercent) were added. The tube was evacuated and backfilledwith argon for three times, and then 3 mL of dry CH3CN was added through a syringer underargon. The tube was sealed with Parafilm M® and placed in an oil bath with a contact thermometer, and the reaction was carried out at 50 °C under irradiation with 6 × 5 W blue LEDs (λmax = 455nm). After 24 h, the resulting mixture was filtered through a 2 cm thick pad of silica, and the silicawas washed with DCM) (50 mL). The filtrate was collected and the solvent was removed in vacuo.The crude residue was purified by silica gel flash column chromatography to provide the targetproduct (2). (Note: The reaction was very sensitive to moisture, and the yields sharply decreased to less than 5percent when 0.01 equivalent of H2O was added to the reaction system).

Molecular Weight:205.00
XLogP3:1.8
Hydrogen Bond Acceptor Count:1
Exact Mass:204.93885
Monoisotopic Mass:204.93885
Topological Polar Surface Area:12.9
Heavy Atom Count:7
Complexity:56
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes