Category: 167884-17-5

Application of 167884-17-5 ,Some common heterocyclic compound, 167884-17-5, molecular formula is C8H8N2O, 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.

i) Synthesis of 3-(imidazo[1,2-a]pyridin-5-yl)methylthiazolidine-2,4-dione To a suspension of 1.19 g (8.0 mmol) of 5-hydroxymethylimidazo[1,2-a]pyridine in 10 ml of dichloromethane, 4.05 ml (56 mmol) of thionyl chloride was added, followed by stirring at room temperature for 1 hour, after which the solvent was distilled off. To a solution of this residue and 0.94 g (8.0 mmol) of thiazolidine-2,4-dione in 15 ml of N,N-dimethylformamide, 2.40 ml (16.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by stirring at 80 C. for 16 hours. After the reaction mixture was cooled, water was added; the mixture was extracted with ethyl acetate and dried, after which the solvent was distilled off. The residue was purified by recrystallization (solvent, chloroform/ethyl acetate/diethyl ether) to yield 247 mg (12.5%, light brown powder) of the desired product. 1 H-NMR (CDCl3, 200 MHz) delta 4.02 (2H, s), 5.06 (2H, s), 6.98 (1H, d, J=6.6 Hz), 7.18 (1H, dd, J=7.0, 9.0 Hz), 7.66 (1H, d, J=9.0 Hz), 7.70 (1H, d, J=1.0 Hz), 7.89 (1H, s)

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. 167884-17-5, Imidazo[1,2-a]pyridin-5-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries Ltd.; US5840732; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 167884-17-5 ,Some common heterocyclic compound, 167884-17-5, molecular formula is C8H8N2O, 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.

i) Synthesis of 3-(imidazo[1,2-a]pyridin-5-yl)methylthiazolidine-2,4-dione To a suspension of 1.19 g (8.0 mmol) of 5-hydroxymethylimidazo[1,2-a]pyridine in 10 ml of dichloromethane, 4.05 ml (56 mmol) of thionyl chloride was added, followed by stirring at room temperature for 1 hour, after which the solvent was distilled off. To a solution of this residue and 0.94 g (8.0 mmol) of thiazolidine-2,4-dione in 15 ml of N,N-dimethylformamide, 2.40 ml (16.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by stirring at 80 C. for 16 hours. After the reaction mixture was cooled, water was added; the mixture was extracted with ethyl acetate and dried, after which the solvent was distilled off. The residue was purified by recrystallization (solvent, chloroform/ethyl acetate/diethyl ether) to yield 247 mg (12.5%, light brown powder) of the desired product. 1 H-NMR (CDCl3, 200 MHz) delta 4.02 (2H, s), 5.06 (2H, s), 6.98 (1H, d, J=6.6 Hz), 7.18 (1H, dd, J=7.0, 9.0 Hz), 7.66 (1H, d, J=9.0 Hz), 7.70 (1H, d, J=1.0 Hz), 7.89 (1H, s)

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. 167884-17-5, Imidazo[1,2-a]pyridin-5-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries Ltd.; US5840732; (1998); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 167884-17-5, Adding some certain compound to certain chemical reactions, such as: 167884-17-5, name is Imidazo[1,2-a]pyridin-5-ylmethanol,molecular formula is C8H8N2O, 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 167884-17-5.

(5) Imidazo[1,2-a]pyridine-5-carbaldehyde Ethyl imidazo[1,2-a]pyridine-5-carboxylate (824 mg) was dissolved in methylene chloride (40 mL). Diisobutylaluminum hydride (1 M solution in toluene) (5 mL) was added at -78C and the mixture was stirred at – 78C for two hours. Diisobutylaluminum hydride (1 M solution in toluene) (10 mL) was further added to the mixture, followed by stirring at -78C for two hours. Methanol (1 mL) was added to the reaction mixture at – 78C, followed by addition of a 20% (+)-potassium sodium tartrate solution. After stirring at room temperature, the reaction mixture was filtered through celite and washed with methylene chloride, followed by extraction with methylene chloride twice. The organic layers were combined, washed with a saturated sodium chloride solution and then dried over magnesium sulfate. The drying agent was removed by filtration and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in acetone (15 mL). 80% manganese dioxide (3 g) was added and the mixture was stirred at room temperature for 11 hours and 20 minutes. The reaction mixture was filtered and washed with acetone. The solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-methanol) to obtain the title compound (96 mg). 1H-NMR (400 MHz, CDCl3) delta(ppm): 7.35-7.44 (m, 1H), 7.53 (d, J=6.8 Hz, 1H), 7.88 (s, 1H), 7.99 (d, J=8.8 Hz, 1H) , 9.04 (s, 1H) , 9.92 (s, 1H) .

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. 167884-17-5, Imidazo[1,2-a]pyridin-5-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2017275; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 167884-17-5, Adding some certain compound to certain chemical reactions, such as: 167884-17-5, name is Imidazo[1,2-a]pyridin-5-ylmethanol,molecular formula is C8H8N2O, 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 167884-17-5.

(5) Imidazo[1,2-a]pyridine-5-carbaldehyde Ethyl imidazo[1,2-a]pyridine-5-carboxylate (824 mg) was dissolved in methylene chloride (40 mL). Diisobutylaluminum hydride (1 M solution in toluene) (5 mL) was added at -78C and the mixture was stirred at – 78C for two hours. Diisobutylaluminum hydride (1 M solution in toluene) (10 mL) was further added to the mixture, followed by stirring at -78C for two hours. Methanol (1 mL) was added to the reaction mixture at – 78C, followed by addition of a 20% (+)-potassium sodium tartrate solution. After stirring at room temperature, the reaction mixture was filtered through celite and washed with methylene chloride, followed by extraction with methylene chloride twice. The organic layers were combined, washed with a saturated sodium chloride solution and then dried over magnesium sulfate. The drying agent was removed by filtration and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in acetone (15 mL). 80% manganese dioxide (3 g) was added and the mixture was stirred at room temperature for 11 hours and 20 minutes. The reaction mixture was filtered and washed with acetone. The solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-methanol) to obtain the title compound (96 mg). 1H-NMR (400 MHz, CDCl3) delta(ppm): 7.35-7.44 (m, 1H), 7.53 (d, J=6.8 Hz, 1H), 7.88 (s, 1H), 7.99 (d, J=8.8 Hz, 1H) , 9.04 (s, 1H) , 9.92 (s, 1H) .

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. 167884-17-5, Imidazo[1,2-a]pyridin-5-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2017275; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 167884-17-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 167884-17-5, name is Imidazo[1,2-a]pyridin-5-ylmethanol. A new synthetic method of this compound is introduced below.

To a solution of imidazo[l,2-a]pyridin-5-ylmethanol (0.150 g, 1.01 mmol, 1 eq) in DMF (2 mL) was added ethyl 3-bromopropanoate (367 mg, 2.02 mmol, 2 eq), NaOH (121 mg, 3.04 mmol, 3 eq) and TBAI (3.74 mg, 0.010 mmol, 0.01 eq). The mixture was stirred for 16 h at 50C. The reaction was quenched with water (10 mL), the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgS04 and concentrated in vacuo. The residue was purified by prep-TLC (Si02, DCM/MeOH = 10/1, Rf = 0.42) to give ethyl 3-(imidazo[l,2-a]pyridin-5-ylmethoxy)propanoate (0.04 g, 13% yield, 80% purity) as a yellow oil, LCMS: m/z = 249.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,167884-17-5, Imidazo[1,2-a]pyridin-5-ylmethanol, and friends who are interested can also refer to it.

Reference:
Patent; PIPELINE THERAPEUTICS, INC.; XIONG, Yifeng; SCHRADER, Thomas; CHEN, Austin; ROPPE, Jeffrey Roger; BACCEI, Jill Melissa; BRAVO, Yalda; (199 pag.)WO2019/241131; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem