Month: May 2021

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. 612-55-5, name is 2-Iodonaphthalene, A new synthetic method of this compound is introduced below., Formula: C10H7I

A mixture of 1,1-dibromo-1,2,2,2-tetrafluoroethane (260 mg), magnesium powder (50 mg) and tetrahydrofuran was added to a three-necked flask equipped with a stirrer and a condenser and replaced with nitrogen. 5 C After the reaction was stirred for 24 hours, the reaction was complete to obtain a solution of a trifluorovinylmagnesium complex. The solution was heated to 40 C and 2-iodonaphthalene (300 mg) and tetrakis (triphenylphosphine palladium) (11.5 mg) were added and the reaction was continued for 6 hours. The column was passed through n-hexane to give a colorless liquid, Yield 90%.

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; Beijing Yuji Science And Technology Co., Ltd.; Chen Chaohui; Jia Xiaoqing; Quan Hengdao; (5 pag.)CN106866355; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, 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. category: iodides-buliding-blocks

General procedure: A two-necked 200-mL round-bottomed flask equipped with a magnetic stirring bar was charged with aryl iodide 17 (1.733 g, 5.083 mmol), CuI (20.8 mg, 0.109 mmol), and DMF (25 mL). To the solution were added Et3N (2.1 mL, 15.1 mmol), PdCl2(PPh3)2 (36.1 mg, 0.0514 mmol), and trimethylsilylacetylene (1.1 mL, 7.8 mmol). The solution was stirred for 30 h. The reaction was quenched with water, and the mixture was extracted with EtOAc three times. The combined organic extracts were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to leave the residue, which was purified by short silica gel column chromatography (hexanes-EtOAc= 9 : 1) to afford TMS-acetylene (1.706 g, 5.49 mmol, quant.) as yellow solids; Rf=0.74 (Silica gel, hexanes-EtOAc= 3 : 1). A 100-mL round-bottomed flask equipped with a magnetic stirring bar was charged with TMS-acetylene and MeOH (10 mL). To the solution was added K2CO3 (1.4 g, 10.1 mmol) at 0 C. The solution was stirred for 10 min. The solution was concentrated under reduced pressure. The reaction mixture was filtered through a pad of Celite. The filter cake was washed with ether, and the filtrate was concentrated under reduced pressure to leave the residue, which was purified by silica gel column chromatography (hexanes-ether= 9 : 1) to afford aryl acetylene 18 (909 mg, 3.80 mmol, 75 % for 2 steps) as a pale yellow solid;

The synthetic route of 181765-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cho, Hidetsura; Iwama, Yusuke; Okano, Kentaro; Tokuyama, Hidetoshi; Chemical and Pharmaceutical Bulletin; vol. 62; 4; (2014); p. 354 – 363;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 63262-06-6, name is 1,4-Dibromo-2,5-diiodobenzene, molecular formula is C6H2Br2I2, 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 C6H2Br2I2

Under the protection of nitrogen, 4.85 g of compound II, 2.50 g of trimethylsilylacetylene, 50 ml of triethylamine, 100 mg of cuprous iodide and 150 mg of dichlorobis(triphenylphosphine)palladium were added.Block the reaction system, stir at room temperature overnight, gas phase detectionReaction process, after the reaction is over,The triethylamine was distilled off under reduced pressure, and the column was eluted with a solvent of n-hexane to afford a crude product.White solid 3.2 g, yield 80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 63262-06-6, its application will become more common.

Reference:
Patent; Henan Academy Of Sciences Chemical Institute Co., Ltd.; Zhou Yang; Zhao Yongde; Dai Bencai; Liu Changchun; Wang Lantian; Zhang Yuli; Chai Cuncai; Chen Jieying; (11 pag.)CN108558948; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 175278-11-2, These common heterocyclic compound, 175278-11-2, name is 1-Bromo-3,5-difluoro-2-iodobenzene, 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.

Step 3. Ethyl 2-(2′-bromo-4′,6′-difluoro-2,3,4,5-tetrahydro-[l,l’-biphenyl]-4-yl)acetate. In a sealed microwave tube, a mixture of ethyl 2-[4-(tetramethyl-l,3,2-dioxaborolan-2- yl)cyclohex-3-en-l-yl] acetate (200 mg, 0.68 mmol), [1,1′- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (24.9 mg, 0.03 mmol), l-bromo-3,5- difluoro-2-iodobenzene (260 mg, 0.82 mmol) and sodium carbonate (0.85 mL, 2.0 M, 1.7 mmol) in dioxane (3.40 mL) was heated at 70C for 20 h. Upon completion of the reaction, the reaction mixture was filtered through celite, washed thoroughly with EtOAc, and purified via flash chromatography (0-20% EtOAc/heptanes) to obtain the title compound as a colorless oil (210 mg, 86%). 1H NMR (400 MHz, CDCb) d 7.13 (td, /= 2.0, 8.1 Hz, 1H), 6.78 (dt, / = 2.5, 8.8 Hz, 1H), 5.60 (d, / = 1.7 Hz, 1H), 4.17 (q, / = 7.2 Hz, 2H), 2.45 – 2.31 (m, 3H), 2.22 – 2.12 (m, 1H), 2.00 – 1.84 (m, 2H), 1.63 – 1.50 (m, 1H), 1.48 (s, 2H), 1.28 (t, / = 7.1 Hz, 3H). [M+H] = 361.0.

Statistics shows that 1-Bromo-3,5-difluoro-2-iodobenzene is playing an increasingly important role. we look forward to future research findings about 175278-11-2.

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 148870-57-9, 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. 148870-57-9 name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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.

Example 6 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one Based on EP 0 534 859 A solution of the (d) camphorsulphonate salt obtained in Example 5 in ethyl acetate is brought to basic pH using sodium hydroxide and then the organic phase is separated off, washed, dried over Na2SO4 and evaporated. A mixture composed of 5.6 g of potassium carbonate, 2.2 g of the above amine in 100 mL of acetone and 4 g of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is then refluxed for 18 hours. The solvent is evaporated off in vacuo, and the residue is taken up in ethyl acetate and then extracted with 3N hydrochloric acid. The aqueous phase separated off is brought to basic pH using sodium hydroxide and is then extracted with ethyl acetate. After washing until neutral and drying over MgSO4, evaporation in vacuo is carried out to obtain 4.5 g of an oil which is purified on a silica column using a mixture of dichloromethane/methanol (90/10) as eluant. Yield=64%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Les Laboratoires Servier; Vaysse-Ludot, Lucile; Le Flohic, Alexandre; Vaultier, Michel; Pucheault, Mathieu; Kaminski, Thomas; US8859763; (2014); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 71838-16-9,Some common heterocyclic compound, 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, molecular formula is C7H6BrI, 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: Method B: To a 10 mL sealed vial was added Cu(OAc)2·H2O (20 mg, 0.1 mmol), N-methoxy-1H-pyrrole-2-carboxamide (14 mg, 0.1mmol), aryl halide (1.0 mmol), aminobenzenethiol (1.2 mmol), KOH (224 mg, 4.0 mmol), PEG-100 (2.0 g) and a magnetic stir bar. The reaction mixture was stirred in an oil bath preheated to 90 C for 15 h. After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 × 40 mL) and water (40 mL). The combined organic phases were washed with brine, dried overanhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-iodo-4-methylbenzene, its application will become more common.

Reference:
Article; Huang, Manna; Hou, Jianying; Yang, Ruiqiao; Zhang, Liting; Zhu, Xinhai; Wan, Yiqian; Synthesis; vol. 46; 24; (2014); p. 3356 – 3364;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 660-49-1, A common heterocyclic compound, 660-49-1, name is 3-Fluoro-5-iodoaniline, molecular formula is C6H5FIN, 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.

A solution of 3-fluoro-5-iodoaniline (250 mg, 1.055 mmol) and dihydro-2H- pyran-4(3H)-one (264 mg, 2.637 mmol) in methanol (5 mL) was charged into a 25 mL round bottom flask with a magnetic stir bar. Acetic acid (0.121 mL, 2.11 mmol) was added and the resulting solution was stirred for 30 minutes at room temperature. Sodium cyanoborohydride (133 mg, 2.11 mmol) was added, the resulting solution was stirred overnight at room temperature. The reaction was quenched with 10 mL 1M aqueous NaOH, stirred for 15 minutes. The solution was extracted with EtOAc (3 x 15 mL), the combined organic layers were washed with brine (15 mL), dried with MgS04, filtered, and evaporated under vaccuum. The crude product was dry loaded onto 3 g. silica and purified by column chromatography (ISCO normal phase, 24 g. gold column, 0-60% EtOAc/hexanes gradient) to isolate N-(3-fluoro-5-iodophenyl)tetrahydro-2H-pyran-4- amine (047) (208 mg, 0.648 mmol, 61%). 1H NMR (400 MHz, CDCb) d ppm 1.41 – 1.55 (m, 2 H) 1.95 – 2.09 (m, 2 H) 3.38 – 3.48 (m, 1 H) 3.53 (td, 7=11.61, 2.13 Hz, 2 H) 3.65 – 3.80 (m, 1 H) 4.02 (br d, 7=11.54 Hz, 2 H) 6.20 – 6.30 (m, 1 H) 6.73 (br d, 7=1.76 Hz, 2 H). LCMS: 322.6 [M+H]+.

The synthetic route of 660-49-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COOK, Andrew; REYNOLDS, Dominic; ZHONG, Cheng; BRAWN, Ryan; ELLERY, Shelby; SAMARAKOON, Thiwanka; LIU, Xiang; PRAJAPATI, Sudeep; SHEEHAN, Megan; LOWE, Jason T.; PALACINO, James; (378 pag.)WO2019/200100; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 2996-30-7, 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. 2996-30-7, name is 3-Fluoro-4-iodonitrobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 36A N-(2-Fluoro-4-nitrophenyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-4-amine A solution of 260 mg (1.77 mmol) of 1-methyl-1H-pyrrolo[2,3-b]pyridine-4-amine, 566 mg (2.12 mmol) of 2-fluoro-1-iodo-4-nitrobenzene, 81 mg (0.09 mmol) of tris(dibenzylidene-acetone)dipalladium, 98 mg (0.18 mmol) of 1,1′-bis(diphenylphosphino)ferrocene and 238 mg (2.47 mmol) of sodium tert-butoxide in 8 ml of degassed toluene is stirred at 100 C. overnight. After cooling to RT, the reaction mixture is applied directly to a silica gel column and separated (mobile phase: cyclohexane/ethyl acetate 10:1 to 1:1). Yield: 210 mg (42% of theory) LC-MS (Method 8): Rt=1.89 min. MS (ESI pos.): m/z=287 (M+H)+. 1H-NMR (DMSO-d6, 300 MHz): delta=3.80 (s, 3H), 6.48 (d, 1H), 6.83 (d, 1H), 7.35 (dd, 1H), 7.40 (d, 1H), 8.03 (d, 1H), 8.13 (d, 1H), 8.18 (d, 1H), 9.32 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 3-Fluoro-4-iodonitrobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer HealthCare AG; US2008/269268; (2008); 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 34270-90-1 as follows. SDS of cas: 34270-90-1

Ethyl 2-(5-chloro-6-(2,2,2-lrifluoroethoxy)-4′-(lTifluoromethyl)biphenyl-3- y])acetate (0.4 g, 3.4 mrao) was dissolved in anhydrous DMF (30mL), NaH (60% wt. in paraffin oil, 0,163 g, 6.8 rnmol) was added at 0C. The reaction mixture was stirred for 30 rnin at room temperature and l-iodo-2-(2-iodoethoxy)ethane (1.2 g, 3.7 rnmol) was added drop wise at 0 C. The reaction mixture was stirred an additional 1h at 0 C and saturated NH4C1 solution (lOmL) was added. The reaction mixture was extracted with EtOAc (3x20mL) and the combined organic phases were washed with water (3x20mL) and brine (20mL), and dried over MgS04. The volatiles were removed under reduced pressure and the residue was purified by flash column chromatography to yield ethyl 4-(5-chloro-6- (2,2,2-trifiuoroethoxy)~4′-(trifluorornecarboxylate (400 mg).

According to the analysis of related databases, 34270-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; KOENIG, Gerhard; BLAIN, Jean-francois; WO2013/106328; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 39998-81-7, A common heterocyclic compound, 39998-81-7, name is 2-Fluoro-4-iodo-1-methylbenzene, molecular formula is C7H6FI, 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.

Example 7: (Compound N7)2-Amino-l-ethyl-7-((R)-3-hydroxy-4-methoxy-3-methyl-but-l-ynyl)-3- (lH-imidazol-2-yl)-lH-quinolin-4-one7.1: 2-Fluoro-4-iodo-benzoic acid13.39 g (84.74 mmol) potassium permanganate were added to a suspension of 5 g (21.18 mmol) of 2-fluoro-4-iodo-toluene and 25.13 g (317.77 mmol) of pyridin in water. The mixture was heated and stirred at 70C during 18 hours. As the reaction was not finished, 3.34 g (21.18 mmol) of potassium permanganate were added to the reaction mixture at room temperature and the mixture was stirred for another 6 hours at 70C. The reaction mixture was then filtered through a celite pad, which was then washed with water and ethyl acetate. After decantation, the aqueous phase was acidified to pH =1 with an aqueous solution of HC1 6N. A white solid was first filtered and the aqueous phase extracted three times with ethyl acetate. The combined organic phases were dried over MgS04 and the solvents were evaporated off under reduced pressure. The filtered white solid and the solid extracted with ethyl acetate were combined to give 4.1 g.Yield = 73%.MH+ = 266.9 (C7H4FI02). 1H NMR (DMSO-d6, 400MHz): delta 13.49 (broad signal, 1H); 7.88 (d, 1H); 7.78 (d, 1H); 7.65 (d, 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; SANOFI; BRAUN, Alain; DUCLOS, Olivier; LASSALLE, Gilbert; LORGE, Franz; MARTIN, Valerie; RITZELER, Olaf; STRUB, Aurelie; WO2012/159959; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com