Category: 49674-15-9

Some common heterocyclic compound, 49674-15-9, name is 3-Bromo-5-nitrobenzonitrile, molecular formula is C7H3BrN2O2, 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. SDS of cas: 49674-15-9

Example 96 -(2,4-dimethoxypyrimidin-5-yl)-4-((3-((4-fluorophenyl)amino)-5-(2H-tetrazol-5- yl)phenyl)amino)quinoline-3-sulfonamide 3-((4-fluorophenyl)amino)-5-nitrobenzonitrile. To a suspension of 3-bromo-5- nitrobenzonitrile (500 mg, 2.202 mmol), 4-fluoroaniline (245 mg, 2.202 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1 ,1 ‘-biphenyl]-2-yl)phosphine (105 mg, 0.220 mmol) and cesium carbonate (1076 mg, 3.30 mmol) in ferf-butanol (2 ml.) and toluene (10 ml.) was added palladium(ll) acetate (9.89 mg, 0.044 mmol). The mixture was heated in a microwave synthesiser at 120 C for one hour. After cooling, the reaction was filtered and organic solvent was removed under reduced pressure. The resulting brown oil was purified by flash chromatography (silica gel, 0-100% ethyl acetate in hexanes) to afford 3-((4-fluorophenyl)amino)-5- nitrobenzonitrile (355 mg, 1.380 mmol, 62.7 % yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) ppm 7.19 – 7.30 (m, 4 H) 7.60 (dd, J=2.27, 1.26 Hz, 1 H) 7.89 (t, J=2.15 Hz, 1 H) 7.94 – 7.99 (m, 1 H) 9.06 (s, 1 H). LCMS (ES+) m/e 258 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 49674-15-9, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROWN, Kristin, K.; CHAI, Deping; DODSON, Christopher, S.; DUFFY, Kevin, J.; SHAW, Antony, Nicholas; WO2013/96151; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 49674-15-9, name is 3-Bromo-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3BrN2O2

To a stirring solution of 845 mg (3.72 mmol) of 3-bromo-5-nitrobenzonitrile in 5 rnL of THF and 5 rnL of EtOH was added 4.2 g (18.6 mmol) of SnCl22H2O in several portions.The reaction became slightly exothermic and was stirred at r.t. for about 12.5 h. The mixture was concentrated and 30 mL of 2 N NaOH was added. After the mixture was stirred for 2 h,H2O and EtOAc were added, and the organic layer was washed with 50 mL of H2O and 40 mL of brine. The aqueous layer was extracted with EtOAc and washed with brine. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (35% EtOAc/hexanes) provided 461 mg of 3-amino-5- bromobenzonitrile as a yellow solid in 63% yield.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 49674-15-9, name is 3-Bromo-5-nitrobenzonitrile, belongs to nitriles-buliding-blocks 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 49674-15-9, HPLC of Formula: C7H3BrN2O2

General procedure: To a solution of 6 (500 mg, 2.64 mmol) in 10 mL of DMF was successively added Et3N (1.47 mL, 10.56 mmol), 9a (600 mg, 2.64 mmol), CuI (50 mg, 0.26 mmol), and trans-dichlorobis(triphenylphosphine)palladium (184 mg, 0.26 mmol). The resulting solution was warmed to 60 oC, and TBAF 1M in THF (2.9 ml, 2.90mmol) was added dropwise. After 2h at this temperature the mixture was hydrolyzed with 50 mL of H2O and, extracted with AcOEt (4 X 30 mL). The organic layer was washed with saturated NaCl (3 X 30 mL), dry over anhydrous Na2SO4, and concentrated on a rotary evaporator. Purification of the residue by column chromatography (hexane/AcOEt 8/2) yielded 473 mg (68 %) of 2a as an off white solid.1H NMR (CDCl3), d = 2.50 (s, 3H, CH3); 7.13 (d, 1H, J=7.6 Hz, CHAr); 7.32 (d, 1H, J=7.6 Hz, CHAr); 7.56 (t, 1H, J=7.6 Hz, CHAr); 8.04 (t, 1H, J=1.6 Hz, CHAr); 8.35 (t, 1H, J=1.6 Hz, CHAr); 8.52 (t, 1H, J=1.6 Hz, CHAr). 13C NMR (CDCl3), d = 24.5 (1C, CH3); 83.4 (1C, C?C); 93.6 (1C, C?C); 114.4 (1C, Cq); 115.9 (1C, Cq); 124.4 (1C, CHAr); 124.9 (1C, CHAr); 126.1 (1C, Cq); 126.4 (1C, CHAr); 130.3 (1C, CHAr); 136.7 (1C, CHAr); 140.1 (1C, CHAr); 140.7 (1C, Cq); 148.1 (1C, Cq); 159.5 (1C, Cq). Anal (C15H9N3O2, HCl) C, H, N.

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, 3-Bromo-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3243 – 3247;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 49674-15-9 as follows. Recommanded Product: 3-Bromo-5-nitrobenzonitrile

To a stirring solution of 1.8 g of 3-bromo-5-nitrobenzonitrile in 8 mL of EtOH and 8 mL of THF was added 8.8 g (38.6 mmol) of SnCl22H2O in several portions. The mixture was allowed to stir at r.t. for 10.5 h and then concentrated. A solution of 2N NaOH (60 mL) was added and stirring continued for 2 h. EtOAc was added, and the layers were separated. The organic layer was washed with H2O and brine. The aqueous layer was reextracted with EtOAc and washed with brine. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (35% EtOAc/hexanes) provided 965 mg of 3-amino-5-bromobenzonitrile.

According to the analysis of related databases, 49674-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts