Synthetic Route of 25676-75-9, The chemical industry reduces the impact on the environment during synthesis 25676-75-9, name is 4-Bromo-1-methylimidazole, I believe this compound will play a more active role in future production and life.
To a suspension of tert-butyl 4-({[2-amino-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (I-55) (1 1 .08 g, 27.2 mmol), 4-bromo-1 -methyl-1 H-imidazole (5.26 g, 32.7 mmol), Cs2C03 (2 N in H20, 27.2 mL, 54.5 mmol) in toluene (50 mL) and EtOH (150 mL) was added Pd(PPh3)4 (4.72 g, 4.08 mmol). The mixture was thoroughly degassed with N2 three times and the brown suspension was then stirred at 85 C for 16 hr under N2. LCMS showed the desired product by mass had formed. The reaction mixture was concentrated under vacuum to give a residue, which was diluted with CH2CI2 (300 mL), washed with water (50 mL), brine (30 mL), dried over Na2S04 and concentrated to give the crude product which was purified twice by silica gel chromatography (0 to 5% MeOH in CH2CI2 followed by CH2CI2/MeOH = 1 /0 to 20/1 ) to give tert-butyl 4-({[2-amino-5-(1 -methyl-1 H-imidazol-4-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (~ 5.9 g as a brown solid. ~ 90% purity). This material was diluted with EtOAc / CH2CI2 (5:1 , 60 mL) and heated to 60 C until a clear solution was obtained. Cooling the solution to 25 C with concomitant reduction of the volume under reduced pressure (~10 mL) lead to the appearance of a precipitate. The suspension was filtered, the filter cake was washed with EtOAc/petroleum ether (1 :1 , 10 mL) and dried under vacuum to give tert-butyl 4-({[2-amino-5-(1 -methyl-1 H-imidazol-4-yl)pyridin-3-yl]oxy}methyl)piperidine-1 -carboxylate (1-106) (4.38 g, 42%) as a purple solid.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-1-methylimidazole, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
Imidazole – Wikipedia,
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