Reference of 6188-23-4 ,Some common heterocyclic compound, 6188-23-4, molecular formula is C7H5BrN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
Example 896-(lmidazo[1,2-a]pyridin-6-ylethynyl)-2,2-dimethyl-2H-pyrano[2,3-b]pyridin-4(3H)- one [00270] A mixture of 6-bromoimidazo[1 ,2-a]pyridine (4.00 g, 20.30 mmol), ethynyltrimethylsilane (2.98 g, 30.30 mmol), PdCI2[PPh3]2 (460 mg, 0.66 mmol), Cul (380 mg, 2.02 mmol), and TEA (8.4 mL, 60.9 mmol) in benzene (25 mL) is stirred at 50 C under argon atmosphere for 8 h, cooled down to r.t. and concentrated at reduced pressure. The obtained residue is purified by column chromatography (silica gel, EtOAc/hexane) to give 6-((trimethylsilyl)ethynyl)imidazo[1 ,2-a]pyridine (3.20 g, 74%) as yellow solid.[00271 ]TBAF solution in THF (1 M, 1 .04 mL, 1 .04 mmol) is added dropwise to a solution of 6-((trimethylsilyl)ethynyl)imidazo[1 ,2-a]pyridine (3.20 g, 14.90 mmol) in THF (20 mL) at 0 C. The resulting mixture is stirred at 0 C for 1 h, diluted with water and extracted with DCM (3×30 mL). The combined organic phases were dried over Na2S04 and concentrated at reduced pressure. The obtained residue was purified by column chromatography (silica gel, EtOAc/hexane) to give 6-ethynylimidazo[1 ,2-a]pyridine (1 .37 g, 65%) as brown oil.[00272]According to General Procedure 1 , 6-bromo-2,2-dimethyl-2/-/-pyrano[2,3- b]pyridin-4(3/-/)-one (256 mg, 1 .0 mmol) is reacted with 6-ethynylimidazo[1 ,2-a]pyridine (156 mg, 1 .1 mmol) in the presence of PdCI2[PPh3]2 (35 mg, 0.05 mmol), P(f-Bu)3 (10 mg, 0.05 mmol), DBU (15 mg, 0.1 mmol), and TEA (2 mL) in acetonitrile (10 mL) at reflux for 6 h. The crude product is purified by column chromatography (silica gel, EtOAc/hexane) to provide the title compound (123 mg, 39%).1H NMR (De-DMSO), deltaEta, 1 .47 (s, 6H), 2.92 (s, 2H), 7.32 (d, 1 H), 7.60 (d, 1 H), 7.64 (s, 1 H), 7.96 (s, 1 H), 8.24 (s, 1 H), 8.66 (s, 1 H), 8.92 (s, 1 H).LC/MS (M+H)+ = 318
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. 6188-23-4, 6-Bromoimidazo[1,2-a]pyridine, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; ABEL, Ulrich; MULLER, Sibylle; KUBAS, Holger; MEYER, Udo; HECHENBERGER, Mirko; KAUSS, Valerjans; ZEMRIBO, Ronalds; WO2012/52451; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem