With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.112197-15-6, name is 3-Iodo-2-methoxypyridine, molecular formula is C6H6INO, molecular weight is 235.02, as common compound, the synthetic route is as follows.Recommanded Product: 112197-15-6
To a stirred, cooled (0C) 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, ZnCl2*TMEDA (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0C before introduction of the substrate (1.0 mmol) at 0-10C. 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 solution of Na2S2O3 (4 mL) and extraction with AcOEt (3×20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. To the crude iodide were added Cs2CO3 (0.65 g, 2.0 mmol), Cu powder (13 mg, 0.20 mmol), the azole (1.5 mmol) and MeCN (5 mL) and the resulting mixture was heated under reflux for 24 h. Filtration over Celite, washing with AcOEt, removal of the solvent and purification by chromatography on silica gel (the eluent is given in the product description) led to the compound described below. 2-Methoxy-3-(1-pyrazolyl)pyridine (1c). The general procedure 1 using 2-methoxypyridine (1a, 0.11 mL) and pyrazole (0.10 mL) gave 1c (eluent: heptane-AcOEt 80:20) in 32% yield as a pale yellow oil: IR (ATR): 752, 795, 933, 1016, 1045, 1105, 1189, 1251, 1304, 1394, 1415, 1471, 1521, 1593, 1736, 2956 cm-1; 1H NMR (CDCl3) d 4.04 (s, 3H), 6.42 (dd, 1H, J 2.5 and 1.8 Hz), 7.00 (dd, 1H,J 7.6 and 5.0 Hz), 7.70 (d, 1H, J 1.4 Hz), 8.07-8.13 (m, 2H), 8.21 (dd,1H, J 2.5 and 0.5 Hz); 13C NMR (CDCl3) d 54.0 (CH3), 106.8 (CH),117.4 (CH), 124.8 (C), 131.3 (CH), 131.8 (CH), 140.8 (CH), 144.3 (CH),154.9 (C); HRMS (ESI): calcd for C9H9N3NaO ([M+Na]) 198.0643, found 198.0641.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,112197-15-6, 3-Iodo-2-methoxypyridine, and friends who are interested can also refer to it.
Reference:
Article; Hedidi, Madani; Erb, William; Bentabed-Ababsa, Ghenia; Chevallier, Floris; Picot, Laurent; Thiery, Valerie; Bach, Stephane; Ruchaud, Sandrine; Roisnel, Thierry; Dorcet, Vincent; Mongin, Florence; Tetrahedron; vol. 72; 41; (2016); p. 6467 – 6476;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem