Category: 578007-66-6

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.578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine, molecular formula is C6H5BrINO, molecular weight is 313.92, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-3-iodo-2-methoxypyridine

Intermediate compound10:ethyl 2-(5-bromo-2-methoxypyridin-3-yl)-5,5-dimethylcyclohex-1-enecarboxylate[360]Starting material8(1.14 g, 3.70 mmol), 5-bromo-3-iodo-2-methoxypyridine (1.40 g, 4.44 mmol), Pd(PPh3)4(0.85 g, 0.74 mmol) and cesium carbonate (2.41 g, 7.40 mmol) were dissolved in dioxane/water (v/v 9:1, 10 mL), and then reacted by microwave irradiation at 120 for 30 minutes. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate, and then washed with a saturated ammonium chloride solution. The organic layer was dried with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure to remove the solvent. The residue was purified by MPLC (SiO2, EtOAc/hexane = 1:9) to obtain compound10(0.37 g, 27%) as colorless oil.[361]MS (ESI) m/z 368.0 (M++ H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,578007-66-6, 5-Bromo-3-iodo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jae Kwang; OH, Jung Taek; LEE, Jae Won; LEE, Seo Hee; KIM, Il-Hyang; LEE, Jae Young; BAE, Su Yeal; LEE, Se Ra; KIM, Yun Tae; WO2014/119947; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 578007-66-6 , The common heterocyclic compound, 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine, molecular formula is C6H5BrINO, 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.

Step 1: tert-Butyl (1-(4-((5-bromo-2-methoxypyridin-3- yl)ethynyl)phenyl)cyclobutyl)carbamate: To a degassed solution of 5-bromo-3-iodo-2- methoxypyridine (823 mg, 2.62 mmol) in triethylamine (8.0 mL) at 0 C was added Pd(PfBu3)2 (1 10.4 mg, 6 mol%), Cul (5.0 mg, 1 mol%) and terf-butyl (1-(4- ethynylphenyl)cyclobutyl)carbamate (71 1 mg, 2.62 mmol). The brown suspension was stirred for 56 hours at room temperature before the reaction mixture was suspended in dichloromethane and washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (gradient 10 to 25% EtOAc in hexane) to give the title compound as a white solid (1.04 g, 87%). H-NMR (500 MHz, CDCI3) delta 8.14 (d, 1 H), 7.84 (d, 1 H), 7.52 (dd, 2H), 7.41 (d, 2H), 5.13 (bs, 1 H), 4.01 (s, 3H), 2.50-2.56 (m, 4H), 2.09-2.14 (m, 1 H), 1.84-1.90 (m, 1 H), 1.36 (bs, 9H).

The synthetic route of 578007-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMAC DISCOVERY LIMITED; BELL, Mark, Peter; O’DOWD, Colin, Roderick; ROUNTREE, James, Samuel, Shane; TREVITT, Graham, Peter; HARRISON, Timothy; MCFARLAND, Mary, Melissa; WO2011/55115; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 578007-66-6, Adding some certain compound to certain chemical reactions, such as: 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine,molecular formula is C6H5BrINO, 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 578007-66-6.

EXAMPLE 119; N-(2-Methoxy-5-(4-morpholinoquinolin-6-yl)pyridin-3- yl)methanesulfonamide; (1) N-(5-Bromo-2-methoxypyridin-3-yl)methanesulfonamide.; To a 5 mL microwave vial, 5-bromo-3-iodo-2-methoxypyridine (0.317 g, 1.01 mmol, Alfa Aesar, Ward Hill, MA), methanesulfonamide (0.100 g, 1.06 mmol), cesium carbonate (0.829 g, 2.54 mmol) and copper(I) iodide (0.0211 g, 0.111 mmol) were mixed into DMF (1 mL). water (0.1 mL) was added and the mixture was heated at 105 0C for 20 h. The reaction mixture was poured into water/Tris-lM HCl pH 7 buffer then IN HCl was added to bring pH to ~5. The aqueous phase was extracted with EtOAc (3 X 20 mL). The combined organic phases were washed with saturated aqueous NaCl (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (eluent: EtOAc in hexanes 0 % – 50 %) to afford an off white solid (0.135 g) as the desired product. MS (ESI pos. ion) m/z calcd for C7H9BrN2O3S: 280.0; found 280.8/282.8 [M+l/M+3]. 1H NMR (300 MHz, CHLOROFORM-^), delta ppm 3.04 (s, 3 H) 3.92 – 4.07 (m, 3 H) 6.74 (br. s., 1 H) 7.89 (d, J=2.19 Hz, 1 H) 7.97 (d, J=2.19 Hz, 1 H).

According to the analysis of related databases, 578007-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2009/155121; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 578007-66-6, Adding some certain compound to certain chemical reactions, such as: 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine,molecular formula is C6H5BrINO, 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 578007-66-6.

EXAMPLE 119; N-(2-Methoxy-5-(4-morpholinoquinolin-6-yl)pyridin-3- yl)methanesulfonamide; (1) N-(5-Bromo-2-methoxypyridin-3-yl)methanesulfonamide.; To a 5 mL microwave vial, 5-bromo-3-iodo-2-methoxypyridine (0.317 g, 1.01 mmol, Alfa Aesar, Ward Hill, MA), methanesulfonamide (0.100 g, 1.06 mmol), cesium carbonate (0.829 g, 2.54 mmol) and copper(I) iodide (0.0211 g, 0.111 mmol) were mixed into DMF (1 mL). water (0.1 mL) was added and the mixture was heated at 105 0C for 20 h. The reaction mixture was poured into water/Tris-lM HCl pH 7 buffer then IN HCl was added to bring pH to ~5. The aqueous phase was extracted with EtOAc (3 X 20 mL). The combined organic phases were washed with saturated aqueous NaCl (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography (eluent: EtOAc in hexanes 0 % – 50 %) to afford an off white solid (0.135 g) as the desired product. MS (ESI pos. ion) m/z calcd for C7H9BrN2O3S: 280.0; found 280.8/282.8 [M+l/M+3]. 1H NMR (300 MHz, CHLOROFORM-^), delta ppm 3.04 (s, 3 H) 3.92 – 4.07 (m, 3 H) 6.74 (br. s., 1 H) 7.89 (d, J=2.19 Hz, 1 H) 7.97 (d, J=2.19 Hz, 1 H).

According to the analysis of related databases, 578007-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2009/155121; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 578007-66-6, 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. 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-3-iodo-2-methoxypyridine (50 g, 159 mmol) in toluene (1000 mL) was added phenylmethanethiol (17.8 g, 143 mmol), DIPEA (55.6 mL, 319 mmol), XantPhos (7.37 g, 12.74 mmol). The mixture was degassed with argon for 10 mm then Pd(dba)2 (4.58 g, 7.96 mmol) was added and the reaction mixture was stirred at 70 C for 1 h. The reaction mixture was filtered through celite,washing with EtOAc (200 mL) and the filtrate was concentrated in vacuo. The crude material was purified by normal phase column chromatography on silica eluting with 5% EtOAc in petroleum ether. The appropriate fractions were combined and concentrated in vacuo to afford the title compound (90 g) as a solid.LCMS (Method D) Rt = 2.68 mi [M+H] = 308.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,578007-66-6, 5-Bromo-3-iodo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; BARTON, Nicholas Paul; CAMPOS, Sebastien Andre; CANNONS, Edward Paul; COOPER, Anthony William James; DOWN, Kenneth David; DOYLE, Kevin James; HAMBLIN, Julie Nicole; HENLEY, Zoe Alicia; INGLIS, Graham George Adam; LE GALL, Armelle; PATEL, Vipulkumar Kantibhai; PEACE, Simon; SHARPE, Andrew; WHITE, Gemma Victoria; (129 pag.)WO2019/20657; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 578007-66-6, 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. 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-3-iodo-2-methoxypyridine (50 g, 159 mmol) in toluene (1000 mL) was added phenylmethanethiol (17.8 g, 143 mmol), DIPEA (55.6 mL, 319 mmol), XantPhos (7.37 g, 12.74 mmol). The mixture was degassed with argon for 10 mm then Pd(dba)2 (4.58 g, 7.96 mmol) was added and the reaction mixture was stirred at 70 C for 1 h. The reaction mixture was filtered through celite,washing with EtOAc (200 mL) and the filtrate was concentrated in vacuo. The crude material was purified by normal phase column chromatography on silica eluting with 5% EtOAc in petroleum ether. The appropriate fractions were combined and concentrated in vacuo to afford the title compound (90 g) as a solid.LCMS (Method D) Rt = 2.68 mi [M+H] = 308.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,578007-66-6, 5-Bromo-3-iodo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; BARTON, Nicholas Paul; CAMPOS, Sebastien Andre; CANNONS, Edward Paul; COOPER, Anthony William James; DOWN, Kenneth David; DOYLE, Kevin James; HAMBLIN, Julie Nicole; HENLEY, Zoe Alicia; INGLIS, Graham George Adam; LE GALL, Armelle; PATEL, Vipulkumar Kantibhai; PEACE, Simon; SHARPE, Andrew; WHITE, Gemma Victoria; (129 pag.)WO2019/20657; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 578007-66-6, 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. 578007-66-6, name is 5-Bromo-3-iodo-2-methoxypyridine. A new synthetic method of this compound is introduced below.

To a solution of 5-bromo-3-iodo-2-methoxypyridine (50 g, 159 mmol) in toluene (1000 mL) was added phenylmethanethiol (17.8 g, 143 mmol), DIPEA (55.6 mL, 319 mmol), XantPhos (7.37 g, 12.74 mmol). The mixture was degassed with argon for 10 mm then Pd(dba)2 (4.58 g, 7.96 mmol) was added and the reaction mixture was stirred at 70 C for 1 h. The reaction mixture was filtered through celite,washing with EtOAc (200 mL) and the filtrate was concentrated in vacuo. The crude material was purified by normal phase column chromatography on silica eluting with 5% EtOAc in petroleum ether. The appropriate fractions were combined and concentrated in vacuo to afford the title compound (90 g) as a solid.LCMS (Method D) Rt = 2.68 mi [M+H] = 308.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,578007-66-6, 5-Bromo-3-iodo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ANDERSON, Niall Andrew; BARTON, Nicholas Paul; CAMPOS, Sebastien Andre; CANNONS, Edward Paul; COOPER, Anthony William James; DOWN, Kenneth David; DOYLE, Kevin James; HAMBLIN, Julie Nicole; HENLEY, Zoe Alicia; INGLIS, Graham George Adam; LE GALL, Armelle; PATEL, Vipulkumar Kantibhai; PEACE, Simon; SHARPE, Andrew; WHITE, Gemma Victoria; (129 pag.)WO2019/20657; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem