Category: 909720-21-4

Allcock, Robert W.’s team published research in Bioorganic & Medicinal Chemistry Letters in 2011 | CAS: 909720-21-4

2,3-Dibromo-6-methoxypyridine(cas: 909720-21-4) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Electric Literature of C6H5Br2NO

Electric Literature of C6H5Br2NOOn June 1, 2011, Allcock, Robert W.; Blakli, Haakon; Jiang, Zhong; Johnston, Karen A.; Morgan, Keith M.; Rosair, Georgina M.; Iwase, Kazuhiko; Kohno, Yasushi; Adams, David R. published an article in Bioorganic & Medicinal Chemistry Letters. The article was 《Phosphodiesterase inhibitors. Part 1: Synthesis and structure-activity relationships of pyrazolopyridine-pyridazinone PDE inhibitors developed from ibudilast》. The article mentions the following:

Ibudilast [1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one] is a nonselective phosphodiesterase inhibitor used clin. to treat asthma. Efforts to selectively develop the PDE3- and PDE4-inhibitory activity of ibudilast led to replacement of the iso-Pr ketone by a pyridazinone heterocycle. Structure-activity relationship exploration in the resulting 6-(pyrazolo[1,5-a]pyridin-3-yl)pyridazin-3(2H)-ones revealed that the pyridazinone lactam functionality is a critical determinant for PDE3-inhibitory activity, with the nitrogen preferably unsubstituted. PDE4 inhibition is strongly promoted by introduction of a hydrophobic substituent at the pyridazinone N(2) center and a methoxy group at C-7′ in the pyrazolopyridine. Migration of the pyridazinone ring connection from the pyrazolopyridine 3′-center to C-4′ strongly enhances PDE4 inhibition. These studies establish a basis for development of potent PDE4-selective and dual PDE3/4-selective inhibitors derived from ibudilast. In addition to this study using 2,3-Dibromo-6-methoxypyridine, there are many other studies that have used 2,3-Dibromo-6-methoxypyridine(cas: 909720-21-4Electric Literature of C6H5Br2NO) was used in this study.

2,3-Dibromo-6-methoxypyridine(cas: 909720-21-4) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Electric Literature of C6H5Br2NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Brief introduction of 2,3-Dibromo-6-methoxypyridine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,909720-21-4, 2,3-Dibromo-6-methoxypyridine, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 909720-21-4, 2,3-Dibromo-6-methoxypyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, SDS of cas: 909720-21-4, blongs to pyridine-derivatives compound. SDS of cas: 909720-21-4

1,4-Dioxane (450 mL) and water (150 mL) were added to a mixture of 2,3- dibromo-6-methoxypyridine (12 g, 45 mmol), C2 (31.8 g, 135 mmol), di(l -adamantyl)- ?- butylphosphine (cataCXium A; 3.22 g, 8.98 mmol), palladium(ll) acetate (3.03 g, 13.5 mmol), and cesium carbonate (87.9 g, 270 mmol), and the reaction vessel was evacuated and charged with nitrogen. This evacuation cycle was repeated twice, and the reaction mixture was then stirred at reflux for 20 hours. After the reaction mixture had been partitioned between ethyl acetate (300 mL) and saturated aqueous sodium chloride solution (200 mL), the aqueous layer was extracted with ethyl acetate (2 x 200 mL); the combined organic layers were washed with saturated aqueous sodium chloride solution (200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was treated with triethylamine (3 mL), dissolved in dichloromethane and treated with silica gel; this mixture was concentrated to dryness and used for silica gel chromatography (Gradient: 0% to 6% ethyl acetate in petroleum ether) to afford the product as a brown oil. Yield: 10 g, 27 mmol, 60%. LCMS m/z 388.0 [M+Na+]. 1H NMR (400 MHz, CDCI3) delta 7.39 (d, J=8.3 Hz, 1H), 6.52 (d, J=8.3 Hz, 1H), 4.63 (dd, J=4.0, 2.8 Hz, 1H), 4.58 (dd, J=4.0, 2.8 Hz, 1H), 4.19-4.1 1 (m, 1H), 3.94-3.71 (m, 4H), 3.89 (s, 3H), 3.58-3.42 (m, 3H), 3.05 (t, J=7.2 Hz, 2H), 2.89 (t, J=7.2 Hz, 2H), 1.86-1.74 (m, 2H), 1.74-1.64 (m, 2H), 1.62-1.44 (m, 8H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,909720-21-4, 2,3-Dibromo-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; CHAPPIE, Thomas Allen; HENDERSON, Jaclyn Louise; YOUNG, Joseph Michael; WAGER, Travis T.; KORMOS, Bethany Lyn; PATEL, Nandini Chaturbhai; SCIABOLA, Simone; TUTTLE, Jamison Bryce; VERHOEST, Patrick Robert; TUCKER, Joseph Walter; (181 pag.)WO2017/122116; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem