Category: 58139-04-1

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 58139-04-1, name is 2-Iodo-3-methoxypyrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Iodo-3-methoxypyrazine

Intermediate 25 (0.15 g, 0.622 mmol) was dissolved in 1,4-dioxane (6 mL). 2-Iodo-3-methoxypyrazine (0.12 g, 0.508 mmol), cesium carbonate (0.405 g, 1.244 mmol, 1,1′-bis(diphenylphosphino)ferrocene (0.052 g, 0.093 mmol) and tris(dibenzylideneacetone) dipalladium(0) (0.028 g, 0.031 mmol) were added. The reaction tube was sealed and the mixture was stirred at 160 C. for 1 hour under microwave irradiation. After cooling, the reaction mixture was diluted with DCM and filtered over dicalite. The filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography (silica gel; eluent: 7 M solution of ammonia in methanol/DCM 0/100 to 5/95). The desired fractions were collected and concentrated. This crude was further purified by preparative HPLC on (Chiralpal Diacel AS 20*250 mm) Mobile phase (CO2, MeOH with 0.2% iPrNH2) to yield compound 8 (0.010 g, 5% yield).

According to the analysis of related databases, 58139-04-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Gijsen, Henricus Jacobus Maria; Van Brandt, Sven Franciscus Anna; US2014/364428; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 58139-04-1 as follows. Recommanded Product: 2-Iodo-3-methoxypyrazine

Intermediate 25 (0.15 g, 0.622 mmol) was dissolved in 1,4-dioxane (6 mL). 2-Iodo-3- methoxypyrazine (0.12 g, 0.508 mmol), cesium carbonate (0.405 g, 1.244 mmol, Iota, – bis(diphenylphosphino)ferrocene (0.052 g, 0.093 mmol) and tris(dibenzylideneacetone) dipalladium(0) (0.028 g, 0.031 mmol) were added. The reaction tube was sealed and the mixture was stirred at 160 C for 1 hour under microwave irradiation. After cooling, the reaction mixture was diluted with DCM and filtered over dicalite. The filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography (silica gel; eluent: 7 M solution of ammonia in methanol/DCM 0/100 to 5/95). The desired fractions were collected and concentrated. This crude was further purified by preparative HPLC on (Chiralpal Diacel AS 20x250mm). Mobile phase (C02, MeOH with 0.2% iPrNH2) to yield compound 8 (0.010 g, 5% yield).

According to the analysis of related databases, 58139-04-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GIJSEN, Henricus, Jacobus, Maria; VAN BRANDT, Sven, Franciscus, Anna; WO2013/83556; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 58139-04-1, name is 2-Iodo-3-methoxypyrazine, belongs to pyrazines compound, 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 58139-04-1, COA of Formula: C5H5IN2O

Step 1: tert-Butyl (1-(4-((3-methoxypyrazin-2-yl)ethynyl)phenyl)cyclobutyl)carbamate: To a degassed solution of 2-iodo-3-methoxypyrazine (163 mg, 0.69 mmol) intriethylamine (1.5 mL) at 0 C was added Pd(P’Bu3)2 (14.1 mg, 6 mol%), Cul (1.8 mg, 2 mol%) and fert-butyl (1 -(4-ethynylphenyl)cyclobutyl)carbamate (125 mg, 0.46 mmol). The brown suspension was stirred for 6 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 0 to 25% EtOAc in hexane) to give the title compound as a white solid (124 mg, 47%). 1H-NMR (500 MHz, CDCI3) delta 8.15 (s, 1 H), 8.04 (s, 1 H), 7.60 (d, 2H), 7.44 (d, 1 H), 5.30 (bs, 1 H), 4.1 1 (s, 3H), 2.51 -2.56 (m, 4H), 2.09-2.14 (m, 1 H), 1.84-1.91 (m, 1 H), 1.37 (bs, 9H).

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, 2-Iodo-3-methoxypyrazine, other downstream synthetic routes, hurry up and to see.

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;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 58139-04-1, name is 2-Iodo-3-methoxypyrazine, belongs to Pyrazines compound, 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 58139-04-1, Product Details of 58139-04-1

To a solution of 2-iodo-3-methoxypyrazine (22)9 (118 mg, 0.5 mmol) in THF (1 mL) was added isopropylmagnesium chloride (0.3 mL, 0.6 mmol, 2 M in THF) at 0 C. The mixture was stirred for exactly 7 min and a solution of 1,1?-bisindole-3,3?-dicarbaldehyde (14) (29 mg, 0.1 mmol) in THF (1 mL) was added dropwise. The reaction mixture was warmed to room temperature for 18 h and diluted with ethyl acetate (15 mL). The organic solution was washed with water (10 mL) and NH4Cl (10 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography using n-hexanes/ethyl acetate (1:1) as eluent to give diol 16 as a yellow oil (51 mg, 0.098 mmol, 98%) and an inconsequential mixture of diastereomers, which was used immediately in the next step. To a solution of 16 (51 mg, 0.098 mmol) in dichloromethane/acetonitrile (1:2, 5 mL) were added triethylsilane (28 mg, 38.4 muL, 0.24 mmol) and boron trifluoride diethyl etherate (34 mg, 29.6 muL, 0.24 mmol) at 0 C. The reaction mixture was stirred at 0 C for an additional 30 min and diluted with dichloromethane (15 mL). The solution was washed with NaHCO3 (satd, 10 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash column chromatography using ethyl acetate/methanol (19:1) as eluent to give the title compound as a yellow oil (40 mg, 0.084 mmol, 86%); numax (neat)/cm-1 3054, 2947, 2925, 2865, 1540, 1450, 1391, 1310, 1123, 1009, 740; deltaH (400 MHz, CDCl3) 8.05 (2H, d, J 2.8, 2¡ÁArH), 7.96 (2H, d, J 2.8, 2¡ÁArH), 7.77 (2H, d, J 7.4, 2¡ÁArH), 7.19-7.12 (4H, m, 4¡ÁArH), 7.18 (2H, s, 2¡ÁArH), 6.82 (2H, d, J 7.8, 2¡ÁArH), 4.31 (4H, d, J 4.2, 2¡ÁCH2), 3.99 (6H, s, 2¡ÁMe); deltaC (100 MHz, CDCl3) 158.8 (2¡ÁC), 146.1 (2¡ÁC), 138.9 (2¡ÁCH), 137.3 (2¡ÁC), 135.9 (2¡ÁCH), 126.6 (2¡ÁC), 126.3 (2¡ÁC), 123.3 (2¡ÁCH), 120.9 (2¡ÁCH), 119.9 (2¡ÁCH), 112.2 (2¡ÁC), 109.2 (2¡ÁCH), 53.7 (2¡ÁMe), 28.9 (2¡ÁCH2); m/z (ESI) 499 (65%, [M+Na]+), 376 (15), 311 (12), 261 (100); HRMS (ESI, [M+Na]+) found 499.1858. [C28H24N6NaO2]+ requires 499.1853.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-3-methoxypyrazine, and friends who are interested can also refer to it.

Reference:
Article; Wang, Christy; Sperry, Jonathan; Tetrahedron; vol. 70; 21; (2014); p. 3430 – 3439;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

58139-04-1, name is 2-Iodo-3-methoxypyrazine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 2-Iodo-3-methoxypyrazine

Step 1: To a stirred mixture of sodium iodide (4.89 g, 32.67 mmol) and 2-iodo-3-methoxypyrazine (2.57 g,10.89 mmol) in acetonitrile (30 mL) at rt was added trimethylsilyl chloride (3.55 g, 32.67 mmol). The mixture was heatedat 70 C for 1.5 h. The mixture was cooled to rt and partitioned between a mixture of DCM, MeOH, and aq 2 M HCl. Theorganic layer was separated and the aqueous layer was extracted with additional DCM/MeOH mixture. The combinedorganic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to afford 3-iodopyrazin-2(1H)-one (1.21 g, 50%) as a brown solid that did not require further purification. 1H NMR (500 MHz, DMSO-d6) delta 12.54(br s, 1H), 7.42 (d, J = 3.7 Hz, 1H), 7.17 (d, J = 3.7 Hz, 1H); LCMS (ESI) m/z 223 (M+H)+.

The synthetic route of 58139-04-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ambit Biosciences Corporation; HADD, Michael J.; HOCKER, Michael D.; HOLLADAY, Mark W.; LIU, Gang; ROWBOTTOM, Martin W.; XU, Shimin; (299 pag.)EP2766359; (2016); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem