In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 78686-79-0, name is Methyl 5-bromo-2-chloronicotinate, the common compound, a new synthetic route is introduced below. name: Methyl 5-bromo-2-chloronicotinate
12A: Methyl 5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-chloronicotinate : A mixture of N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide (300 mg, 1.424 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (579 mg, 2.279 mmol), PdCl2(dppf)-CH2Cl2 adduct (116 mg, 0.142 mmol) and potassium acetate (419 mg, 4.27 mmol) in dioxane (8 mL) was heated to 100 C for 6 h. The reaction mixture was allowed to cool to rt. To the stirred crude mixture was added methyl 5-bromo-2-chloronicotinate (392 mg, 1.565 mmol) and PdCl2(dppf)-CH2Cl2 adduct (58.1 mg, 0.071 mmol) and the mixture was degassed by bubbling nitrogen though the mixture for 5 min. Potassium carbonate (393 mg, 2.85 mmol) was quickly added and the reaction mixture heated at 100 C for 4 h. An additional 1/2 equivalent of bromide, catalyst and base were added and heating to 100 C was continued for 2 h. The reaction mixture was partitioned between EtOAc (75 mL) and water (75 mL). The organic layer was washed with brine (50 mL), dried (Na2S04) and concentrated to a residue that was chomato graphed on a 40 gm ISCO silica gel cartridge, eluting with a 0-10%MeOH/DCM gradient. The pure fractions were concentrated to afford methyl 5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-chloronicotinate (275 mg, 0.795 mmol, 55.9 % yield) as a yellow solid. 7968 MSESI m z 346.1/348.1 (M+H) NMR (500 MHz, DMSO-d6) delta 10.97 (s, 1H), 9.24 (d, J=2.2 Hz, 1H), 8.85 (d, J=2.5 Hz, 1H), 8.36 (s, 1H), 8.14 (d, J-8.8 Hz, 1H), 7.92 (d, J=9.4 Hz, 1H), 3.94 (s, 3H), 2.12 (s, 3H).
The synthetic route of 78686-79-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MERTZMAN, Michael E.; DZIERBA, Carolyn Diane; GUERNON, Jason M.; HART, Amy C.; LUO, Guanglin; MACOR, John E.; PITTS, William J.; SHI, Jianliang; SPERGEL, Steven H.; (245 pag.)WO2019/89442; (2019); A1;,
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