Category: 101335-11-9

Reference of 101335-11-9, A common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, 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.

General procedure: To 259 mg (26.9 mmol) pyrimidin-5-ol (J. Chem. Soc. 1956, 2033) in 200 mL DMF are added 108 mg (26.9 mmol) sodium hydride (60% dispersion in mineral oil). The mixture is stirred for 20 mm at r.t.. After that time, 500 mg (22.4 mmol) 2-fluoro-4-iodopyridine are added and the mixture is stirred for 12 h at 80 C. Subsequently the mixture is poured into water and extracted with ethyl acetate (3x). The combined organic layers are washed with brine. After drying over sodium sulphate, the solvent is removed in vacuo and the residue is purified by column chromatography (silica gel; heptane/EtOAc, 100/0 – 40/60).C9H6IN3O (M = 299.1 g/mol)ESI-MS: 300 [M+H]+ Rt(HPLC) : 2.87 min (method C) For the example XXVIII.4 6 eq. of the alcohol and 4 eq. of KOtBu as base are used and the reaction mixture is stirred at r.t. for 3 h.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; ROTH, Gerald Juergen; NOSSE, Bernd; HEINE, Niklas; WO2013/92616; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 101335-11-9 as follows. Formula: C6H3ClFI

Step 1. Ethyl 2-(4-(2-chloro-4-fluorophenyl)-4-hydroxycyclohexyl)acetate. A solution of n-butyllithium in hexanes (1.6 M, 81.4 mL, 130 mmol) was added dropwise to a solution of 2- chloro-4-fluoro-l-iodobenzene (16.6 mL, 130 mmol) in tetrahydrofuran (197 mL) at -78C. The reaction mixture was allowed to stir at -78C for 1 h before the addition of ethyl 2-(4- oxocyclohexyl)acetate (19.2 mL, 109 mmol) in one portion. The reaction was allowed to warm to room temperature and stirred at room temperature for 1 h. The reaction was quenched with a saturated solution of ammonium chloride (500 mL) and extracted with EtOAc (3 x 150 mL), combined organics dried (Na2S04) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica, eluting with 0-40% EtOAc in hexanes to yield the product as a colorless oil (26.7 g, 78%). 1H NMR (400 MHz, CDCb) d 7.65 (dd, / = 8.86, 6.30 Hz, 1H), 7.21 – 7.09 (m, 1H), 7.03 – 6.94 (m, 1H), 4.27 – 4.07 (m, 5H), 2.62 – 2.47 (m, 2H), 2.46 – 2.18 (m, 10H), 2.15 – 1.82 (m, 6H), 1.78 – 1.34 (m, 7H), 1.34 – 1.22 (m, 7H). [M-H2O+H] = 283.1.

According to the analysis of related databases, 101335-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DART NEUROSCIENCE, LLC; BASINGER, THOMPSON, Jillian; BOOKSER, Brett; BURLEY, Scott; GARCIA-REYNAGA, Pablo; HUDSON, Andrew; PETERS, Marco; PRATT, Benjamin; THOMPSON, Aaron; TRAN, Joe; VALDEZ, Lino; (211 pag.)WO2019/168866; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 101335-11-9, 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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: (E)-4-(2-(2-Chloro-4-fluorophenyl)-l-(4-(thiazol-5-yl)phenyl)but-l-en-l- yl)benzaldehyde[00394] A mixture of (Z)-4-(2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l-(4-(thiazol-5- yl)phenyl)but-l-en-l-yl)benzaldehyde (99 mg, 0.22 mmol), 2-chloro-4-fluoro-l-iodobenzene (114 mg, 0.44 mmol), Pd(PPh3)2Cl2(15 mg, 0.022 mmol), and KOH (6M, 0.2 mL, 1.32 mmol) in 1,4-dioxane (2.2 mL) was heated to 90C overnight. After cooling, ethyl acetate and brine were added to the reaction mixture and the two layers were separated. The organic layer was washed with more brine, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel to afford 68 mg of a mixture of the title compound (major) and the undesired regioisomer (minor). 1H NMR (400 MHz, DMSO-d6) of major: delta 9.84 (s, 1H), 9.11 (s, 1H), 8.35 (s, 1H), 7.75 (d, 2H), 7.64 (d, 2H), 7.40-7.33 (m, 4H), 7.17 (m, 3H), 2.45 (q, 2H), 0.93 (t, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-4-fluoro-1-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SERAGON PHARMACEUTICALS, INC.; SMITH, Nicholas, D.; GOVEK, Steven, P.; KAHRAMAN, Mehmet; BONNEFOUS, Celine; JULIEN, Jackaline, D.; WO2014/151899; (2014); 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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 101335-11-9

To a solution of 2-chloro-4-fluoroiodobenzene (11.6 g) in THF (80 mL) was added dropwise isopropylmagnesium chloride-lithium chloride complex (1.3M THF solution, 34.8 mL) over 20 min at -78 C., and the mixture was stirred at -15 C. for 1.5 hr. To this mixture was added tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (6.16 g), and the mixture was stirred at room temperature for 48 hr. The reaction was quenched with aqueous ammonium chloride solution at 0 C., and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.41 g). 1H NMR (300 MHz, CDCl3) delta1.46 (9H, s), 1.54-1.71 (2H, m), 1.79-1.94 (2H, m), 2.72-2.94 (2H, m), 3.17-3.31 (1H, m), 4.01-4.19 (2H, m), 7.01-7.09 (1H, m), 7.17 (1H, dd, J=8.5, 2.5 Hz), 7.39 (1H, dd, J=8.6, 5.9 Hz).

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 101335-11-9.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Ikeda, Shuhei; SUGIYAMA, Hideyuki; AIDA, Jumpei; TOKUHARA, Hidekazu; OKAWA, Tomohiro; OGURO, Yuya; NAKAMURA, Minoru; MURAKAMI, Masataka; (71 pag.)US2017/283406; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 101335-11-9, A common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, 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.

[0115] To a stirred solution of (Z)-4-(l-(4-(methoxymethoxy)phenyl)-2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)but-l-en-l-yl)benzaldehyde (12 g, 28.4 mmol, with – 10- 15% of another regioisomer) in 2-methyltetrahydrofuran (120 mL) were added 2-chloro-4- fluoro-l-iodobenzene (5.5 mL, 40.5 mmol) and KOH (45 mL, 3M aqueous solution, 142.2 mmol). The resultant mixture was degassed with argon for 10 min followed by the addition of PdCl2(PPh3)2 (0.7 g, 2.84 mmol). After stirring at 60C for 12 h, the mixture was cooled to rt and quenched with water:EtOAc (1 : 1, 100 mL). The organic layer was separated, washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The crude compound was purified by chromatography (Si02, 10% EtOAc/hexane) to afford (E)-4-(2-(2- chloro-4-fluorophenyl)- 1 -(4-(methoxymethoxy) phenyl) but- 1 -en- 1 -yl)benzaldehyde as a pale yellow solid (6.0 g, 67% with -10-15% of the other regioisomer). Major isomer: XH NMR (400 MHz, CDC1 ) delta 9.84 (s, 1H), 7.55 (d, = 8.0 Hz, 2H), 7.20 – 7.17 (m, 2H), 7.10 (d, = 8.0 Hz, 2H), 7.04 – 6.97 (m, 4H), 6.84 – 6.80 (m, 1H), 5.19 (s, 2H), 3.50 (s, 3H), 2.55 – 2.45 (m, 2H), 0.97 – 0.93 (m, 3H); MS (ESI) m/z 425.19 [M+H]+.

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENO ROYALTIES & MILESTONES, LLC; HUANG, Peter, Qinhua; SLEE, Deborah, Helen; BUNKER, Kevin, Duane; HEGDE, Sayee, Gajanan; HOPKINS, Chad, Daniel; (76 pag.)WO2019/23481; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, 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. Computed Properties of C6H3ClFI

To a solution of 2-chloro-4-fluoro-l-iodo-benzene (3.6 g, 14.3 mmol) and 3-trifluoromethyl-lH-pyrazole (1.9 g, 14.4 mmol) in N,N-dimethylformamide (40 mL) was added potassium carbonate (2.4 g, 17.2 mmol), and the resulting mixture was heated at 135 C for 12 h. The reaction mixture was cooled to room temperature, poured in cold water (80 mL) and extracted with dichloromethane (2 x 40 mL). The combined organic extracts were dried (Na2S04) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with 10% ethyl acetate in hexanes to afford the title compound (4.2 g) as a white solid. lH NMR delta 10.4 (s, 1H), 7.88 (m, 2H), 7.80 (d, 1H), 7.27 (m, 1H), 6.68 (d, 1H). MS (AP+) 373 amu.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 101335-11-9, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; BEREZNAK, James, Francis; GUTTERIDGE, Steven; TAGGI, Andrew, Edmund; REDDY, Ravisekhara, P.; CAMPBELL, Matthew, James; KAR, Moumita; DESAEGER, Johan, A., J.; WO2014/4064; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 101335-11-9, name is 2-Chloro-4-fluoro-1-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 101335-11-9, Product Details of 101335-11-9

Step 1 1-[4-(2-Chloro-4-fluoro-benzoyl)-piperidin-1-yl]-ethanone 2-Chloro-4-fluoro-1-iodobenzol (5 g, 19 mmol) was solved in THF (3 mL) and at -10 C. isopropyl magnesium chloride-lithium chloride (2M in THF) was added dropwise and the mixture stirred for 30 minutes at 0 C. At -10 C. 1-acetyl-isonipecotoyl chloride was added (3.3 g, 18 mmol) solved in THF (2 mL) and the mixture stirred for 10 minutes to -10 C. and 4 h to 0 C. Water was added and the reaction extracted with dichloromethane. Chromatography with Heptane/EtOAc (2:1) gave the desired compound as a clear orange liquid (1.8 g, 33% yield). (m/e): 284.3 (M+H+).

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-Chloro-4-fluoro-1-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gobbi, Luca; Jaeschke, Georg; Luebbers, Thomas; Roche, Olivier; Rodriguez Sarmiento, Rosa Maria; Steward, Lucinda; US2007/197531; (2007); A1;,
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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, A new synthetic method of this compound is introduced below., name: 2-Chloro-4-fluoro-1-iodobenzene

Step I: 2-Chloro-4-fluoroiodobenzene (9.03g, 35.22mmol, 2.00eq), potassium hydroxide solution (4M, 22.01mL,5.00eq) and bis(triphenylphosphine)palladium dichloride (617.94mg, 880.50umol, 0.05eq) were added to a solution of11 (8.30g, 17.61mmol, 1.00eq) in 100mL dimethyltetrahydrofuran. The reaction solution was stirred at 70C undernitrogen atmosphere for 12 hours, then filtered through celite, and the filtrate was washed twice with 100mL brine. Theorganic phase was dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product, which waspurified by silica gel column chromatography (PE:EA=40:1-10:1) to give the product 13 as a yellow solid (4.50g, 5.57mmol,yield 31.65%, purity 58.7%). MS [ESI, M+1]: 474.3.

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; Luoxin Biotechnology (Shanghai) Co., Ltd.; Shandong Luoxin Pharmaceutical Group Stock Co., Ltd.; LU, Jianyu; DING, Charles Z.; HU, Lihong; HE, Huijun; CHEN, Shuhui; DONG, Jiaqiang; WANG, Tie-lin; (124 pag.)EP3434668; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 101335-11-9, A common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, 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.

General procedure: To a 15 mL reaction tube, ArI (1 mmol), (i-Pr)2NEt (2 mmol),DMF (0.5 mL) and 5 mg of PdCl2/PANI were added. The reactionmixture was stirred at 140 C under air for 2.5 h. After the reaction,the catalyst was isolated by centrifugalization, washed by deionized water and ethanol, vacuum dried at 60 C and then reused in the next round of reaction. Organic phase was collected, add saturatedsalt water (2 mL), extracted with ethyl acetate (15 mL), thenthe organic phase was dried with anhydrous Na2SO4. The productwas separated and purified by silica gel column chromatography(eluent: petroleum ether).

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Yanping; Liu, Wanyi; Song, Manrong; Sun, Yanyan; Wang, Gang; Wu, Zhiqiang; Zhan, Haijuan; Journal of Catalysis; vol. 384; (2020); p. 177 – 188;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

101335-11-9, name is 2-Chloro-4-fluoro-1-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. Recommanded Product: 101335-11-9

The 1-(2-chloro-4-fluorophenyl)-2-piperazinone used in the above procedure was prepared as follows: A suspension of 2-piperazinone (1.5 g, 15.0 mmol), 2-chloro-4-fluoro-1-iodobenzene (3.8 g, 15.0 mmol), copper(l) iodide (0.57 g, 3.0 mmol), N,N’-dimethyl-1 ,2- cyclohexanediamine (1.3 g, 6.0 mmol), and potassium phosphate (6.4 g, 44.9 mmol) in 1 ,4-dioxane (20 ml) was heated at reflux (1000C) under argon for 20 hours. The mixture was allowed to cool to room temperature and then diluted with dichloromethane and 0.88M ammonia diluted in water (1 :5). The mixture was extracted into dichloromethane (x3), and then the combined organic extracts were washed with water (x2) and dried over magnesium sulphate. The solvent was evaporated in vacuo and the crude product was purified by flash-silica gel chromatography, eluting with 5% 2M ammonia in methanol in dichloromethane, to give the product 1-(2-chloro-4-fluorophenyl)-2-piperazinone (250mg) as a brown oil which was used without further purification. LC/MS [M+H]+ = 229.

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/53459; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com