Extracurricular laboratory: Synthetic route of 2-Iodo-6-methoxypyridine

The synthetic route of 182275-70-3 has been constantly updated, and we look forward to future research findings.

Related Products of 182275-70-3 , The common heterocyclic compound, 182275-70-3, name is 2-Iodo-6-methoxypyridine, molecular formula is C6H6INO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

tei -Butyl 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2/-/)- carboxylate (Intermediate 7) (395 mg, 1.28 mmol) and Cs2C03 (1.03 g, 3.19 mmol) were added to a solution of 2-iodo-6-methoxypyridine (Intermediate 8) (300 mg, 1.28 mmol) in 1 ,4-dioxane (10 mL) and the resulting mixture was degassed under a nitrogen atmosphere for 20 min. (9,9-Dimethyl-9/-/-xanthene-4,5-diyl)bis(diphenylphosphane) (Xantphos, 36 mg, 0.06 mmol) and palladium(ll) acetate (29 mg, 0.13 mmol) were added and the resulting reaction mixture was stirred at 80 C for 18 h. The solvents were removed in-vacuo and residue was partitioned between H20 (80 mL) and EtOAc (60 mL). The aqueous layer was further extracted with EtOAc (60 mL) and the combined organic layers were dried (Na2S04) and the solvent was removed in-vacuo. The residue was purified by column chromatography (normal phase neutral activated alumina, 10 % to 12 % EtOAc in hexane) to give tert- butyl 6- methoxy-3′,6′-dihydro-2,4′-bipyridine-T(2’/-/)-carboxylate (310 mg, 84 %) as a gum. LCMS (System 3, Method D): m/z 291 (M+H)+ (ESI +ve), at 5.73 min, 202 nm.

The synthetic route of 182275-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEPTARES THERAPEUTICS LIMITED; BROWN, Giles; TEOBALD, Barry; TEHAN, Ben; (77 pag.)WO2019/243851; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem