Category: 2265-91-0

Reference of 2265-91-0, 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 2265-91-0 as follows.

To a solution of 3,5-difluoroiodobenzene (1.12 g) in THF (8 mL) was added isopropylmagnesium chloride (2.0 mol/L, THF) (2.1 mL) under an argon atmosphere in ice salt bath, and the mixture was stirred in ice salt bath for 30 minutes. To the reaction mixture was added dropwise a solution of (R)-1-(tert-butoxycarbonyl)-5-oxopyrrolidine-2-carboxylic acid ethyl (0.546 g) in THF (13 mL) at -40C, and the mixture was stirred at the same temperature for 1.5 hours. To the reaction mixture was added a saturated aqueous solution of ammonium chloride, and the mixture was extracted thrice with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude (2R)-2-{[(tert-butoxy)carbonyl]amino}-5-(3,5-difluorophenyl)-5-oxopentanoic acid ethyl (0.911 g). To a solution of the obtained compound in ethyl acetate (21 mL) was added hydrogen chloride in ethyl acetate (4 mol/L, 10.6 mL), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added slowly a saturated aqueous solution of sodium bicarbonate, and the mixture was extracted thrice with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on amino-silica gel (eluent: n-hexane/ethyl acetate=95/5-70/30) to give the title compound (0.505 g).

According to the analysis of related databases, 2265-91-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; KONDO, Atsushi; MORITA, Naohide; ISHIKAWA, Takehiro; YOSHIDA, Masako; MORIYAMA, Akihiro; WANAJO, Isao; (158 pag.)EP3459941; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2265-91-0, name is 1,3-Difluoro-5-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H3F2I

General procedure: To a solution of tetrabutylammonium bromide (1.100 g, 3.33 mmol), potassium acetate (0.586 g, 3.57 mmol), and palladium acetate (0.025 g, 0.11 mmol) in DMF (20 mL) were added substituted iodobenzene (2.21 mmol) and 4-acetyloxystyrene (2.44 mmol). The reaction mixture was recharged with Argon and stirred at 80C for 5 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford the intermediate substituted (E)-4-styrylphenyl acetate. To a solution of triethylamine (2.0 mL) in MeOH (5 mL) was added substituted (E)-4-styrylphenyl acetate (1.36 mmol). The reaction mixture was stirred at reflux temperaturefor 3 h. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane/methanol, 10:0.3) to afford pure product.

The synthetic route of 2265-91-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Jian-Hua; Yang, Liang; Wu, Si; Liu, Si-Si; Cushman, Mark; Tian, Jing; Li, Nuo-Min; Yang, Qing-Hu; Zhang, He-Ao; Qiu, Yun-Jie; Xiang, Lin; Ma, Cong-Xuan; Li, Xue-Meng; Qing, Hong; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 382 – 392;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 2265-91-0,Some common heterocyclic compound, 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, molecular formula is C6H3F2I, 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.

General procedure: (S)-3-((R)-Hydroxyphenylmethyl)pyrrolidine-1-carboxylic acid t-butyl ester 11a (250 mg, 0.9 mmol), copper(I) iodide (51 mg, 270 mumol), 1,10-phenanthroline (97 mg, 540 mumol) and 2,4-difluoro-1-iodobenzene (216 muL, 1.8 mmol) were combined in a vial under air. Toluene (1.4 mL, 14 mmol) was added, followed by the addition of cesium carbonate (587 mg, 1.8 mmol). Air was bubbled through the mixture, the vial was sealed, and the mixture was heated at 105C for 48 hours. The mixture was filtered through Celite. The Celite was then rinsed with DCM (2 x 15 ml), and the resultant filtrate was concentrated. The resultant oil was treated with 1.25 M of HCl in EtOH (5.8 mL, 7.2 mmol) and stirred overnight. The mixture was concentrated and purified by reverse phase preparative HPLC (10 to 70% CH3CN in water with 0.5% TFA) to yield 76 mg (97% purity, 26% yield) of the title compound as the mono-TFA salt.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Difluoro-5-iodobenzene, its application will become more common.

Reference:
Article; Van Orden, Lori Jean; Van Dyke, Priscilla M.; Saito, D. Roland; Church, Timothy J.; Chang, Ray; Smith, Jacqueline A.M.; Martin, William J.; Jaw-Tsai, Sarah; Stangeland, Eric L.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1456 – 1461;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, A new synthetic method of this compound is introduced below., Safety of 1,3-Difluoro-5-iodobenzene

PotassI.um phosphate (1.9 g, 8.7 mmol), trI.s(dI.benzylI.deneacetone)dI.palladI.um (0.27 g, 0.29 mmol), Xantphos (0.17 g, 0.29 mmol) and 3,5-dI.fluoroI.odobenzene (1.5 g, 6.4 mmol) were addedsuccessI.vely to a mI.xture of ethyl 2-aminothI.azole-4-carboxylate (1.0 g, 5.8 mmol) I.n a mI.xture of 9 ml of toluene and 3 ml of water. The mI.xture was flushed wI.th argon for 20 mins, then heated I.n the mI.crowave to 140 C for 1 h. The reactI.on mI.xture was dI.luted wI.th water and extracted wI.th ethyl acetate. The organI.c layer was washed wI.th saturated aqueous sodI.um bI.carbonate solutI.on and water, drI.ed over magnesI.um sulfate and evaporated under reduced pressure. The resI.due was purI.fI.ed bychromatography on sI.lI.ca gel, usI.ng ethyl acetate and cyclohexane as eluents, to delI.ver ethyl 2-(3,5- dI.fluoroanI.lI.no)thI.azole-4-carboxylate (0.16 g, 0.56 mmol). 1H-NMR (400 MHz, CDCl3): oe = 1.41 (t, 3H), 4.40 (q, 2H), 6.54 (t, 1H), 6.95 (d, 2H), 7.63 (s, 1H)

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; SYNGENTA PARTICIPATIONS AG; JEANMART, Stephane, Andre, Marie; ZAMBACH, Werner; RENDINE, Stefano; LAMBERTH, Clemens; BEAUDEGNIES, Renaud; POULIOT, Martin; BONVALOT, Damien; (73 pag.)WO2017/207362; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, belongs to iodides-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 2265-91-0, name: 1,3-Difluoro-5-iodobenzene

In a nitrogen atmosphere, carbazole and potassium tert-butoxide powder were dissolved in 20 mL of anhydrous dimethyl sulfoxide solution, and after mixing well, the reaction temperature rose to 120 C. After the temperature was stabilized, The solution of 1-iodo-3,5-difluorobenzenein anhydrous dimethyl sulfoxide was heated to 140 C after the dropwise addition, and the reaction time was 2 hours. Among them, 1-iodo-3,5-difluorobenzene, carbazole, and tert-butanol The molar ratio of potassium is 1: 2.1: 2.1; the mixed solution is cooled to room temperature and extracted, dried, and rotary solvent is used to remove excess solvent to obtain a crude product. The crude product was separated and purified by column chromatography to obtain compound DCzB-I. The eluent was chloroform: n-hexane = 1: 10 (volume ratio), and the yield was 75%.

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, 1,3-Difluoro-5-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fuzhou University; Guo Zhiyong; Xiao Hui; Lou Yuheng; Han Mingxi; (11 pag.)CN110272379; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 2265-91-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2265-91-0 name is 1,3-Difluoro-5-iodobenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a flask containing a mixture of 1,3-difluoro-5-iodo-benzene(900 mg, 3.75 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (644 mg, 4.5 mmol) in dioxane (20 mL) was added t-BuONa(720 mg, 7.5 mmol), Pd2(dba)3 (174 mg, 0.19 mmol) and Sphos (156 mg, 0.38 mmol) successively under N2. Then the resulting mixture was heated to 100 C and stuffed overnight. After being cooled to rt, the resulting reaction mixture was diluted with H20 (20 mL) and extracted with EA (50 mL) for three times. The combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give crude 8-(3,5- difluorophenyl)-1,4-dioxa-8-azaspiro[4.5]decane (900 mg), which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Difluoro-5-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 2265-91-0, 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 2265-91-0 as follows.

Step 1: tert-Butyl 4-(3,5-difluorophenyl) piperazine-1-carboxylate A solution of tert-butyl-piperazine-1-carboxylate (1.024 g, 5.5 mmol), 1,3-difluoro-5-iodobenzene (1.58 g, 6.6 mmol), t-BuONa (790 mg, 8.25 mmol), BINAP (137 mg, 0.22 mmol), Pd2(dba)3 (100 mg, 0.11 mmol) in dry toluene (40 mL) was stirred under N2 at 80 C. for 16 hrs. The reaction mixture was concentrated and the residue was purified by chromatography (silica, EtOAc/PE=1/10) to afford 1-(3,5-difluorophenyl)piperazine (1.5 g, 5.03 mmol, 91%) as a yellow oil. ESI-MS (EI+, m/z): 243.2 [M-55]+.

According to the analysis of related databases, 2265-91-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (136 pag.)US2019/389843; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 2265-91-0,Some common heterocyclic compound, 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, molecular formula is C6H3F2I, 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.

Compound SM (2g, 8.3mmol),CuI (100 mg, 0.5 mmol) and Pd(PPh3) 2Cl2 (350 mg, 0.5 mmol)Add to the three-necked flask, after replacing N2 three times,DMF (20 ml) and trimethylethynyl silicon (1.31 g, 13.3 mmol) were added.Replace with N2 and finally add triethylamine (1.35 g, 13.3 mmol).After the N2 substitution, the mixture was stirred at 70 C for 3 hours. After complete reaction,The system was cooled to room temperature, filtered through celite, and the filtrate was diluted with water.Extract with ethyl acetate, combine the organic phases, and wash with water.Wash once with saturated brine, dry over anhydrous sodium sulfate, filtered, and then evaporated.The oil was purified by column chromatography to give ((3,5-difluorophenyl)ethynyl)trimethylsilane (1.56 g, yield: 90%, brown oil).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Difluoro-5-iodobenzene, its application will become more common.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Gang; Luo Xiaoyong; Dong Zhenwen; Li Xiaoyong; Yu Hua; Zeng Hong; Song Hongmei; Wang Ying; Wang Lichun; Wang Jingyi; (49 pag.)CN109293652; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2265-91-0, name is 1,3-Difluoro-5-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 1,3-Difluoro-5-iodobenzene

A solution of feri-butyl piperazine- l-carboxylate (2 g, 17.54 mmol), l,3-difluoro- 5-iodobenzene (4.2 g, 17.50 mmol), NaOtBu (2.5 g), BINAP (108 mg, 0.17 mmol), and Pd2(dba)3 (160 mg, 0.17 mmol) in toluene (20 mL) was stirred for 16 h at 80 C, then quenched by the addition of 40 mL FLO. The resulting solution was extracted with 2×40 mL of EtOAc, and the combined organic layers were concentrated under vacuum and purified with silica gel chromatography using EtOAc / hexane (1/2) to afford 3.1 g (59%) of the title compound as an off-white solid. LC-MS: (ES, m/z) 299 NMR (400 MHz, DMSO -d6) d 6.69 – 6.57 (m, 2H), 6.49 (tt, J = 9.3, 2.2 Hz, 1H), 3.42 (t, J = 5.3 Hz, 4H), 3.26 – 3.13 (m, 4H), 1.42 (s, 9H).

The synthetic route of 2265-91-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTAURUS THERAPEUTICS; ROMERO, Donna, L.; BLITZER, Jeremy; (242 pag.)WO2019/140188; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, belongs to iodides-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 2265-91-0, SDS of cas: 2265-91-0

8-methyl-6-phenyl-2H-[2,7]naphthyridine-l-one (200 mg, 0.846 mmol), CuI (32 mg, 0.169 mmol), K 3 PO 4 (359 mg, 1.692 mmol) were suspended in 1,4-dioxane (3 mL), dropwisely added with 3,5-difluoroiodobenzene(0.12 mL, 1.016 mmol), N,N – dimethylethylene diamine (0.036 mL, 0.338 mmol) and then refluxed for 15 hours under nitrogen atmosphere. The resultant was cooled down to room temperature, added with distilled water (50 mL) and then extracted with EtOAc (50 mL). The resulting organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by a silica gel column chromatograph (20% EtOAc/Etaexanes) and obtained a white solid [212 mg(72%)].[139] lambda Eta NMR(300 MHz, CDCl3) delta 3.16(s, 3H), 6.53(d, IH, J=7.2Hz), 6.88-6.95(m,IH), 6.98-7.06(m, 2H), 7. 27(d, IH, J=I. 2Hz), 7.43-7.55(m, 3H), 7.63(s, IH), 8.11-8.15(m, 2H).

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, 1,3-Difluoro-5-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SK CHEMICALS CO., LTD.; WO2006/112666; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com