Brief introduction of 17570-98-8

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, 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, HPLC of Formula: C7H7Br2NO, blongs to pyridine-derivatives compound. HPLC of Formula: C7H7Br2NO

General Procedure 2: Formation of an imidazole by sequential treatment of an amidine with LiHMDS and a heteroaryl-halomethylketone in THF followed by dehydration of the intermediate hvdroxyimidazoli?e in hot acetic acid.; A 1.0 M solution of LiHMDS in THF (Aldrich Chemical Co., 1.0-1.2 equiv, or 2.2 equiv when the heteroaryi-halomethyfketone is a hydrobromide salt) is added dropwise to a solution of the amidine (1.0 equiv) in anhydrous THF (generally 2-4 mL/mmol amidine) at -20 0C to 50C under nitrogen and the resulting solution stirred at about 0 0C for 10-30 min. A solution of the haloketo?e (1.0-1.5 equiv, in equal or greater amount relative to the lithium base) in anhydrous THF (1-3 mL per mmol) is added in one portion. The resulting mixture is stirred in an ice bath for 10-30 min and then at RT for at least 30 min. Water and organic solvent (usually EtOAc or DCM) are added and the product is isolated by extraction into the organic layer which is dried and concentrated. The resulting crude product, which generally contains hydroxy-imidazoline, the target imidazole, and unreacted amidine (HPLCMS analysis) is dissolved in acetic acid (5-25 mUmmol) and heated at 60-1000C for 20-60 min (HPLCMS showing disappearance of the hydroxy-imidazoline peak). This mixture is concentrated, and the crude product isolated by extraction using aqueous NaOH and organic solvent (usually EtOAc or DCM), and residual amidine removed by washing with aqueous citric acid. If not otherwise specified, the product was purified by SGC (gradient of MeOH in DCM, 0.5% NH4OH). In the following Example section, compounds of formula I are designated as Example 1, Example 2, and so on, whereas the corresponding synthetic intermediates are designated Preparation 1 A , Preparation 1 B, or Preparation 2A; Example 4; i-(4-(4-fpvridin-2-vO-1 -fpyrimidin-5-vl)-1 H-imidazol-2-vltohenvl)-1 H-pvrrolof2.3-biDvridine; According to General Procedure 2, NI-(pyrimidi?-5-yl)-4-(1H-pyrrolo[2l3-b]pyridin-1- yl)benzamidine (447 mg, 1.42 mmol) and 2-bromo-1-(pyridin-2-yl)ethanone hydrobromide (400 mg, 1.42 mmol) gave the title substance as a yellow solid. Yield 80 mg, 13.5% of theory. 1H NMR (CDCI3) delta 9.24 (s, 1H), 8.77 (s, 2H)1 8.58 (m, 1H), 8.35 (del, 1H1 J = 1.7, 4.6), 8.13 (d, 1H, J = 7.9), 7.95 (dd, 1H, J =1.5, 7.7), 7.90 (s, 1H), 7.87 (m, 2H), 7.77 (m, 1H), 7.57 (m, 2H), 7.52 (d, 1H, J = 3.7), 7.20 (m, 1H), 7.13 (dd, 1H1 J = 5.0, 7.9), 6.64 (d, 1H, J = 3.7). MS (AP+) m/beta 416 (MH+). IC50 = 13.6 nM

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17570-98-8, 2-(Bromoacetyl)pyridine hydrobromide, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/4117; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem