Category: 856851-48-4

Synthetic Route of 856851-48-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.856851-48-4, name is 2-Chloro-5-ethoxypyridine, molecular formula is C7H8ClNO, molecular weight is 157.6, as common compound, the synthetic route is as follows.

2-Chloro-5-ethoxy-pyridine (23 mg, 0.134 mmol) was dissolved in 2 ml dioxane. To this solution was added under argon 1,3-bis-(2,6-diisopropylphenyl)-imidazolinium chloride (12 mg,0.028 mmol), Pd2dba3 (12 mg, 0.013 mmol), compound (II) (56 mg, 0.143 mmol) and NaOtBu (20 mg, 0.21 mmol). The mixture was heated under argon at 100 C. for 6 hours. After cooling, the reaction was diluted with ethylacetate, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by Prep TLC using 5% methanol in dichloromethylene to afford 23 mg of 6-Dimethylamino-2-{3-[5-(5-ethoxymethyl-pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl]-2-hydroxymethyl-phenyl}-3,4-dihydro-2H-isoquinolin-1-one (31% yield).

The chemical industry reduces the impact on the environment during synthesis 856851-48-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Berthel, Steven; Firooznia, Fariborz; Fishlock, Daniel; Hong, Jun-Bae; Lou, Yan; Lucas, Matthew; Owens, Timothy D.; Sarma, Keshab; Sweeney, Zachary Kevin; Taygerly, Joshua Paul Gergely; US2010/222325; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 856851-48-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 856851-48-4 as follows.

Hydrogen peroxide-urea complex (31 .04 g, 330 mmol) was added in one portion to a solution of 2-chloro-5-ethoxypyridine (26.0 g, 1 65 mmol) in dichloromethane (250 mL) at 0 00 then trifluoroaceticanhydride (62.4 g, 297 mmol, 41 .3 0 mL) was added dropwise. The mixture was stirred at 20 00 for 16 h. The reaction mixture was quenched by addition of saturated aqueous sodium thiosulfate (150 mL). The mixture was extracted with dichloromethane (200 mL x 3), then the combined organic phases were washed with saturated aqueous sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give a crude residue that was purified by chromatography (silica, petroleumether : ethyl acetate 1:0 to 1:2) to give 2-chloro-5-ethoxypyridine 1-oxide (22.0 g, 126.7 mmol, 77%) as a yellow solid. 1H NMR (400 MHz, ODd3) O 8.05 (d, J2.6 Hz, 1 H), 7.29 (d, J9.0 Hz, 1 H), 6.81 (dd, J2.6, 9.1 Hz, 1 H), 3.97 (q, J6.9 Hz, 2H), 1 .37 (t, J7.0 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,856851-48-4, its application will become more common.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 856851-48-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 856851-48-4 as follows.

Hydrogen peroxide-urea complex (31 .04 g, 330 mmol) was added in one portion to a solution of 2-chloro-5-ethoxypyridine (26.0 g, 1 65 mmol) in dichloromethane (250 mL) at 0 00 then trifluoroaceticanhydride (62.4 g, 297 mmol, 41 .3 0 mL) was added dropwise. The mixture was stirred at 20 00 for 16 h. The reaction mixture was quenched by addition of saturated aqueous sodium thiosulfate (150 mL). The mixture was extracted with dichloromethane (200 mL x 3), then the combined organic phases were washed with saturated aqueous sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give a crude residue that was purified by chromatography (silica, petroleumether : ethyl acetate 1:0 to 1:2) to give 2-chloro-5-ethoxypyridine 1-oxide (22.0 g, 126.7 mmol, 77%) as a yellow solid. 1H NMR (400 MHz, ODd3) O 8.05 (d, J2.6 Hz, 1 H), 7.29 (d, J9.0 Hz, 1 H), 6.81 (dd, J2.6, 9.1 Hz, 1 H), 3.97 (q, J6.9 Hz, 2H), 1 .37 (t, J7.0 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,856851-48-4, its application will become more common.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem