Category: 2265-91-0

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., Quality Control of 1,3-Difluoro-5-iodobenzene

Example 1.93: Preparation of 2-(((lr,4r)-4-((3-(3,5-Difluorophenyl)-3- phenylureido)methyl)cyclohexyl)methoxy)acetic Acid (Compound 44).; Step A: Preparation of 3,5-Difluoro-iV-phenylaniline.; In a 5 mL microwave reaction vial was placed aniline (0.298 g. 3.20 mmol) and 1,3- difluoro-5-iodobenzene (0.768 g, 3.20 mmol) in toluene (3 mL). KOH (0.323 g, 5.76 mmol) in water (650 muL) and N,N,N-trimethylhexadecan-l-ammium bromide (6.30 mg, 0.017 mmol) were added to the vial with stirring. After the reaction was warmed to 90 0C, bis[tri(f- butylphosphine]palladium[0] (0.016 g, 0.032 mmol) was added and the reaction was stirred at 150 0C for 4 h and then 160 0C for 2 h. The mixture was diluted with water and brine, and extracted with toluene. The toluene extract was subsequently washed with water, dried over MgSO4 and concentrated. The residue was purified by flash column chromatography to provide the title compound as a brown oil (0.132 g). LCMS m/z = 206.2 [M+H]+; 1H nuMR (400 MHz, DMSO-J6) delta ppm 6.54 (tt, J= 9.35, 2.27 Hz, IH), 6.63 (dd, J= 10.48, 2.15 Hz, 2H), 7.01 (dt, 7 = 14.65, 1.14 Hz, IH), 7.17 (dd, J= 8.59, 1.01 Hz, 2H), 7.34 (t, J= 7.83 Hz, 2H), 8.69 (s, IH).

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; ARENA PHARMACEUTICALS, INC.; WO2009/117095; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature 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.

A mixture of 8-{[tert-butyl(dimethyl)silyl]oxy}-2-azaspiro[4.5]decan-1-one (isomer 1 ) (425 mg, 1 .50 mmol), 1,3-difluoro-5-iodobenzene (360 mg, 1 .50 mmol, CAS No 2265-91-0), copper(l) iodide (143 mg, 0.750 mmol), N,N’-dimethylethylenediamine (164 muIota, 1 .50 mmol) and potassium carbonate (435 mg, 3.15 mmol) in dioxane (26 ml) was heated to 160 for 2 h in a microwave reactor. Upon cooling, the reaction mixture was filtrated through a pad of celite, and the filtrate was concentrated and the residue was purified by flash chromatography (25 g Snap Cartrige, hexanes/ethyl acetate-gradient, 0% -> 50% ethyl acetate) to give the title compound as single isomer (575 mg).LC-MS (Method 2): Rt= 1 .79 min; MS (ESIpos): m/z = 396.3 [M+H]+1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 7.50-7.41 (m, 2H), 6.98-6.91 (m, 1H), 3.94-3.88 (m, 1H), 3.72 (t, 2H), 2.00-1 .85 (m, 4H), 1 .63-1 .47 (m, 4H), 1 .28-1.20 (m, 2H), 0.85 (s, 9H), 0.01 (s, 6H)

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); 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, Product Details of 2265-91-0

General procedure: o-hydroxy-cinnamate ester 1 (0.5 mmol,), aryl iodides 2 (1.0 mmol, 2.0 equiv), Pd(OAc)2 (0.05 mmol, 10 mol %), and H2O (1ml) was charged into a pressure tube. The reaction mixture was stirred at 100 C for 12 h under air. After cooled to room temperature, the reaction mixture was diluted with EtOAc (5 mL) and washed with NH4Cl (3 x 5 mL). The organic phase was separated, dried over NaSO4 and the solvent was removed in vacuo. The residue was purified by column chromatography by using hexanes/ethyl acetate as eluent to afford the desired products 3a-z.

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:
Article; Chen, Junmin; Liu, Wei; Zhou, Liandi; Zhao, Yongli; Tetrahedron Letters; vol. 59; 26; (2018); p. 2526 – 2531;,
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.

Intermediate 4: Ethyl 1-(3,5-difluorophenyl)-5-methyl-1/-/-1 ,2,3-triazole-4-carboxylate; To a mixture of 1 ,3-difluoro-5-iodobenzene (0.2 g, 0.833 mmol) and ethyl 2- butynoate (0.097 ml, 0.833 mmol) in water/DMSO (0.22ml/2ml) at room temperature was added L-proline (0.019 g, 0.167 mmol), sodium carbonate (0.018 g, 0.167 mmol), sodium azide (0.065 g, 1.000 mmol), sodium l-ascorbate (0.017 g, 0.083 mmol) and copper(ll) sulfate pentahydrate (10.40 mg, 0.042 mmol) (in this order) and the mixture was heated at 65C overnight. Monitoring by LC/MS revealed starting material to be present and so the temperature was increased to 100 degrees and the mixture was heated overnight at lOOdegC. On cooling to room temperature, the mixture was quenched with aqueous ammonia (1 ml) and EtOAc (20ml) and water (20 ml) were added. The two phases were separated, and the aqueous phase was extracted with EtOAc (3x 30 ml). All organic phases were combined and washed with water/brine (50ml) repeatedly. The organic phase was dried over sodium sulfate, filtered and the solvent was evaporated to give a crude product that was purified by MDAP to afford the title compound (14.9%); MH+=267.9.

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.

Electric Literature 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: A general procedure for the synthesis of diarylacetylenes 2 involved the addition of 2.0 mmol of arylacetylene to a mixture of 2.1 mmol of an aryliodide, 3.0 mmol of diisoproprylethylamine, 0.02 mmol of Pd(PPh3)4,and 0.02 mmol of CuI in water (7 mL). The mixture was stirred for 1-2 h at 75C. After cooling, the product was collected by filtration or extracted using dichloromethane and purified by recrystallization and/or chromatography.

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.

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, Recommanded Product: 1,3-Difluoro-5-iodobenzene

To a stirred solution of 1 ,3-difluoro-5-iodobenzene (50.0 g, 208.3 mmol) in DMF (250 ml) was added portionwise MeSNa (14.6 g, 208.3 mmol). The reaction was heated at 150C for 1 h. Further MeSNa (1.5 g, 21 mmol) was added and the reaction was stirred at 150C for a further 30 min. The reaction mixture was allowed to cool to rt before being diluted with distilled water (250 ml) and then extracted five times with MTBE (5 x 150 ml). The combined organic layers were then washed three times with brine (3 x 150 ml). The organic layer was dried (MgS04), filtered and concentrated in vacuo to afford a yellow oil (61 g). This oil was combined with 54 g batch from another synthesis to give a combined total of 115 g (429 mmol). This was purified by silica column chromatography (n- heptane) to afford a colourless oil (84.18 g, 76 %). 1 H NMR (CDCI3; 400 MHz): d: 7.31 (s, 1 H), 7.18 (m, 1 H), 6.88 (m, 1 H), 2.45 (s, 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BENEVOLENTAI BIO LIMITED; BROWN, Alan; GLEN, Angela; (115 pag.)WO2020/39209; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H3F2I

General procedure: A general procedure for the synthesis of diarylacetylenes 2 involved the addition of 2.0 mmol of arylacetylene to a mixture of 2.1 mmol of an aryliodide, 3.0 mmol of diisoproprylethylamine, 0.02 mmol of Pd(PPh3)4, and 0.02 mmol of CuI in water (7 mL). The mixture was stirred for 1-2 h at 75 C. After cooling, the product was collected by filtration or extracted using dichloromethane and purified by recrystallization and/or chromatography.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2265-91-0.

Reference:
Article; Sviripa, Vitaliy M.; Zhang, Wen; Kril, Liliia M.; Liu, Alice X.; Yuan, Yaxia; Zhan, Chang-Guo; Liu, Chunming; Watt, David S.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3638 – 3640;,
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.

10297] To a stirred solution of 5-(but-i-yn-i-yl)-i-(tetra- hydro-2H-pyran-2-yl)-1H-indazole (0.4 g, 1.574 mmol, Example 1, Step-3) in 2-methyl THF (5 mE), was added bis(pinacolato)diboron (0.44 g, 1.732 mmol), tetrakis(triphenylphosphine)platinum(0) (14.6 mg, 0.0118 mmol) under nitrogen atmosphere, reaction mixture was heated at 90 C. for 5 h. Afier completion of reaction (monitored by TEC), reaction mixture was allowed to cool to 4 C. and tert-butyl (2-(4-iodophenoxy)ethyl)carbamate (571 mg, 1.574 mmol, Example 3, Step-2), bis(triphenylphosphine)palladium(II) dichloride (55 mg, 0.078 mmol), cesium carbonate (1.023 g, 3.140 mmol) and 2-methyl THF (5 mE) were added. This mixture was degassed with nitrogen and water (1.2 mE) was added. Reaction mixture was stirred at room temperature for 16 h. Afier completion of reaction (monitored by TEC), i,3-difluoro-5-iodobenzene (528 mg, 2.20 mmol) and 4M aqueous KOH (3 mE) were added and the mixture was degassed with nitrogen and heated at 70 C. for 5 h. Upon completion, the reaction mixture was filtered through a celite/silicagel pad and washed with EtOAc. The filtrate was washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (2:8 EtOAc in n-hexane) to give title compound of Ex. 5 Step-i (500 mg, 54%)

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; Eisai R&D Management Co., Ltd.; BOCK, Mark; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (141 pag.)US2016/347717; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2265-91-0, name is 1,3-Difluoro-5-iodobenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C6H3F2I

General procedure: A Schlenk tube with a magnetic stir bar was charged with Pd(OAc)2 (10 mol%, 0.0056 g), AgOTf (1.1 equiv., 0.0707 g), TBAB (20 mol%, 0.0161g), 2-phenylpyridine N-oxides 1 (0.25 mmol), iodobenzene and its derivatives 2 (0.375 mmol) and H2O (1 mL). The resulting solution was stirred at 100C for 12 h. The resulting organic layer was extracted with trichloromethane, treated with Na2SO4 and concentrated in vacuo. The product was isolated by short column chromatography using ethyl acetate and methanol as eluent.

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

Reference:
Article; Zhang, Wei; Li, Zhengkai; Zhang, Yihan; Yang, Li; Zhou, Xiangge; Synthetic Communications; vol. 47; 8; (2017); p. 793 – 802;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2265-91-0, name is 1,3-Difluoro-5-iodobenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 1,3-Difluoro-5-iodobenzene

General procedure: In a microwave tube, 425 mg of (S)-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one (Example 1e) are introduced into 1 ml of dimethylformamide, 422 mg of tripotassium phosphate, 380 mg of copper iodide and 2 ml of iodobenzene. The mixture obtained is heated in a microwave oven for 30 minutes at 150 C. The reaction mixture is then centrifuged. The separated supernatant is then rinsed with ethyl acetate and then evaporated to dryness. The residue is taken up with ethyl acetate and the solution obtained is washed with water. The organic phase is separated and then dried over magnesium sulphate, filtered, and concentrated under vacuum. After purification by silica chromatography (gradient of 5% to 15% of the eluent CH2Cl2/MeOH/NH4OH 28% 38/17/2 in dichloromethane), 150 mg of (8S)-2-(morpholin-4-yl)-9-phenyl-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one are obtained The product is prepared according to the procedure described in Example 12, but using 250 mg of (8S)-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one (Example 1e), 276 mg of 1,3-difluoro-5-iodobenzene, 349 mg of tripotassium phosphate, 156 mg of copper iodide and 93 mg of (1S,2S)-cyclohexane-1,2-diamine. After 1 hour at 150 C. under microwave irradiation and silica column purification of the reaction mixture (elution gradient of CH2Cl2 to CH2Cl2/MeOH 98/02), 91 mg of (8S)-9-(3,5-difluorophenyl)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetra-hydro-4 H-pyrimido[1,2-a]pyrimidin-4-one are obtained in the form of an ochre foam

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

Reference:
Patent; Sanofi; Baku, Eritsuku; Bulolo, Morice; Cross, Annie; El Amado, Youssef; Fuiroshiyu, Lom Brunnow; Array, Frank; Carlson, Carl Andreas; Marciniak, Gilbert; Ronan, Baptiste; Shio, Laulan; Bibe, Bertrand; Viviani, Fabrice; Zimerman, Andre; (90 pag.)JP5655070; (2015); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com