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. 1004294-58-9, name is 6-Bromo-5-chloropyridin-2-amine, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Bromo-5-chloropyridin-2-amine
A solution of N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-5-(2-chloro-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzamido)-1-phenyl-1 H-pyrazole-3-carboxamide (Preparation 7, 500 mg, 0.80 mmol), 6-bromo-5-chloropyridin-2-amine (332 mg, 1.60 mmol) and potassium carbonate (221 mg, 1.60 mmol) in dioxane (10 mL) and water (5 mL) was degassed with nitrogen for 10 minutes before the addition of Pd(PP i3)4 (92 mg, 0.80 mmol). The reaction was heated to reflux for 2 hours. The reaction was diluted with EtOAc (20 mL) and water (20 mL). The aqueous phase was extracted with EtOAc (3 x 20 mL) and the combined organic layers were dried over MgS04 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 40- 60% EtOAc in heptanes and dissolved in THF (2 mL). TBAF (1 M in THF, 96 uL, 0.096 mmol) was added and the reaction stirred at room temperature for 18 hours. The reaction was quenched by the addition of saturated aqueous NH4CI solution (10 mL) and extracted into EtOAc (3 x 10 mL). The combined organic layers were dried over MgS04 and concentrated in vacuo. The residue was purified using reverse phase chromatography eluting with 5-50% MeCN in water with 0.1 % ammonia followed by trituration with MeCN to afford the title compound (8 mg, 8%). 1 H NMR (400MHz, DMSO-d6): delta ppm 3.31-3.35 (2H, m), 3.50 (2H, q), 4.75 (t, 2H), 6.33 (s, 2H), 6.50 (d, 1 H), 6.90 (s, 1 H), 7.45-7.49 (m, 1 H), 7.53-7.62 (m, 5H), 7.70-7.76 (m, 2H), 8.16 (t, 1 H), 10.79 (br s, 1 H). MS m/z 51 1 [M+H]+
The synthetic route of 1004294-58-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; PFIZER INC.; BAGAL, Sharanjeet Kaur; CUI, Jingrong Jean; GREASLEY, Samantha Elizabeth; LUNNEY, Elizabeth Ann; MCALPINE, Indrawan James; NAGATA, Asako; NINKOVIC, Sacha; OMOTO, Kiyoyuki; SKERRATT, Sarah Elizabeth; STORER, Robert Ian; WARMUS, Joseph Scott; WO2015/159175; (2015); A1;,
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