Month: June 2021

Electric Literature of 108078-14-4, 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 108078-14-4 as follows.

A 100-mL RB flask was charged with 2-iodo-3-methylbenzoic acid (1. LG, 4.2 mmol), a stirbar, Et20 (15 mL) and DCM (35 mL) and was cooled to-78 oC under an argon atmosphere. trifluoromethanesulfonic acid (250 uL) was added over 30 sec and isobutylene was bubbled into the solution (until the solution became cloudy) using a 8″/20 gauge steel needle. The reaction was stirred for 6 h between-78 AND-20 oC. Solid NAHCO3 (250 mg) was added and the solution was allowed to warm to rt with stirring. After 20 min, the solution was poured into an extraction funnel containing DCM (50 mL) and NA2C03 (2M, 20 mL). The layers were separated and the organic layer was washed with NA2C03 (2M, 2 x 10 mL), water (20 mL), brine (30 mL) and dried over sodium sulfate. Removal of the solvent in vacuo yielded the title compound (1.05 g, 78%) which was used without further purification. 1H-NMR (CDC13) : delta 7.25 (m, 3H), 2.50 (s, 3H), 1.62 (m, 9H).

According to the analysis of related databases, 108078-14-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-DIMENSIONAL PHARMACEUTICALS, INC.; WO2003/99805; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 5458-84-4,Some common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, molecular formula is C7H6INO3, 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.

Add 1.0 g (3.58 mmol) of 1-iodo-2-methoxy-4-nitrobenzene to a 50 ml two-port bottle and turn on magnetic stirring.Add 15 ml of 95% ethanol at room temperature.Stir for 30min;Adding an appropriate amount of zinc particles to dilute hydrochloric acid for activation;0.8 (12 mmol) of activated zinc particles were sequentially added to the double-mouth bottle.10ml of 20% hydrochloric acid solution,Stirring at room temperature for 72 h;After the reaction,Stop the reaction,The obtained reaction solution was extracted with ethyl acetate.After salt washing, remove the water layer.After the obtained organic phase is distilled under reduced pressure,The dark red solid product, 2-methoxy-4-iodoaniline, 2.18 g was obtained in a yield of 81.23%.

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

Reference:
Patent; Ningxia University; Yang Jinhui; Chi Jiurong; Yan Zhiming; Feng Yueji; Wang Shihaozhi; (5 pag.)CN109776331; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 181765-85-5, 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. 181765-85-5, name is Methyl 4-chloro-2-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of (2-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3- yl)methyl)pyrimidin-5-yl)boronic acid (Intermediate 188c, 45 mg, 0.145 mmol) and methyl 4-chloro-2-iodobenzoate (40 mg, 0.135 mmol ) in THF (1.5 mL) was treated with 1.5 M Na2C03 (0.270 mL, 0.405 mmol) followed by PdCl2(dppf) (5.51 mg, 6.75 muiotaetaomicron). The resulting mixture was degassed with N2 for 2 min before the reaction vessel was sealed and irradiated in a microwave reactor at 100 C for 30 min. The cooled reaction mixture was diluted with DCM and extracted. The combined organic layer was washed with brine, dried over MgS04, and concentrated to dryness and the residue purified by ISCO (Hexanes/AcOEt, 0-100%) to afford the title compound (Intermediate 198a, 36 mg, 0.083 mmol, 61.2 % yield) as a yellow oil. LC-MS (Method A5): 2.20 min, [M + H]+ = 436.1 ; FontWeight=”Bold” FontSize=”10″ H NMR (500 MHz, CDC13) delta 8.59 (s, 1H), 8.67 – 8.44 (m, 1H), 8.03 (d, 7=8.5 Hz, 1H), 7.52 (dd, 7=8.5, 2.2 Hz, 1H), 6.90 (s, 1H), 5.78 (s, 2H), 3.72 (s, 3H), 2.87 (q, 7=7.7 Hz, 2H), 2.67 (s, 3H), 2.59 (s, 3H), 1.39 (t, 7=7.6 Hz, 3H)

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, Methyl 4-chloro-2-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 2974-94-9,Some common heterocyclic compound, 2974-94-9, name is 1-Iodo-4-phenoxybenzene, molecular formula is C12H9IO, 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 3A (R)-3-(4-phenoxyphenoxy)quinuclidine 3-(R)-Hydroxy-quinuclidine (the product of Reference Example 1, 152 mg, 1.2 mmol), was coupled with 1-iodo-4-phenoxy-benzene (178 mg, 0.6 mmol) according to the procedure of Example 3A. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.20) as oil (25 mg, yield, 14%). 1H NMR (MeOH-d4, 300 MHz) delta 1.45-1.58 (m, 1H), 1.64-1.85 (m, 2H), 2.00-2.15 (m, 1H), 2.20-2.30 (m, 1H), 2.70-3.10 (m, 5H), 3.34-3.40 (m, 1H), 4.52 (m, 1H), 6.83-6.98 (m, 6H), 7.03 (tt, J=7.5, 1.0 Hz, 1H), 7.30 (t, J=7.5 Hz, 2H) ppm. MS (DCl/NH3) m/z 296 (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 1-Iodo-4-phenoxybenzene, its application will become more common.

Reference:
Patent; Abbott Laboratories; US2005/137226; (2005); 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. 328-73-4, name is 1-Iodo-3,5-bis(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Iodo-3,5-bis(trifluoromethyl)benzene

Under a nitrogen atmosphere,Alpha-naphthol (7.2 g, 50 mmol),3,5-bis(trifluoromethyl)iodobenzene (20.4 g, 60 mmol),Barium carbonate (19.5 g, 60 mmol) was dissolved in 200 mL DMF.Additional palladium chloride (0.13 g, 0.75 mmol)As a catalyst,Heated at 115 ° C for 12 h,TLC monitors the progress of the reaction.The reaction is over,After falling to room temperature,Extracting the organic phase with ether,Dry over anhydrous MgSO4,filter,concentrate.Column chromatography gave the product as a dark brown oil.It was stirred and reacted with dihydropyran at room temperature for 10 h.A pale yellow solid k with a tetrahydropyran group is obtained.Under a nitrogen atmosphere,The intermediate product k (13.2 g, 30 mmol) was dissolved in 50 mLIn ether,The ice water bath is stable for 5 minutes.Add n-BuLi solution (14 mL, 33 mmol) dropwise.After 0.5 h of reaction, it gradually returned to room temperature.Continue to react for 4h,A large amount of white precipitate l was obtained.6.5 mL of diphenylphosphine chloride (PPh2Cl)Disperse evenly in 10 mL of ether,Under the ice water bath,Add dropwise to the original reaction system,Slowly rise to room temperature,The reaction was stirred overnight.TLC monitoring until the end of the reaction,Quenched with water,Extracting the organic phase with ether,The resulting organic phase was concentrated to 100 mL.Deaeration in the refrigeration cycle,Add 5 mL of concentrated hydrochloric acid under a nitrogen atmosphere.Reaction 5h,The reaction was followed by TLC.Neutralized by adding NaHCO3 aqueous solution,Quenched with water,Extracting the organic phase with ether,Dry over anhydrous MgSO4,filter,concentrate,Flash column chromatography gave 8.1 g of a white solid.The yield was 50percent.

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 328-73-4.

Reference:
Patent; Tianjin University; Li Yuesheng; Wang Xuling; Zhang Yanping; Pan Li; (25 pag.)CN109320558; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 610-97-9, 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. 610-97-9, name is Methyl 2-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred slurry of methyl 2-iodo-benzoate (5.0 g, 0.019 mol) and N-bromosuccinimide (3.74 g, 0.021 mol) in acetic acid (10 ML) was added concentrated H2SO4 (10 ML) dropwise, keeping the temperature at 20-40 C. The mixture was stirred at room temperature for 88 hours and then heated at 50 C. for 4 hours.The mixture was cooled to 10 C., treated with 40 g of ice water, and extracted with 50 ML of CH2Cl2.The organic phase was washed in succession with 2*50 ML 5% NaHCO3, 50 ML 10% Na2S2O3, 50 ML water, and concentrated to colorless oil.The residue was purified by column chromatography (silica gel, 10:90 EtOAc:hexane) to provide the title compound. 1H NMR (CDCl3, 400 MHz) delta 7.92 (d, J=4 Hz, 1H), 7.83 (d, J=8 Hz, 1H), 7.27 (dd, J=8, 4 Hz, 1H), 3.92 (s, 3H); MS (DCl/NH3) [M+NH4]+ at 358, [M+NH3 NH4]+ at 375.

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, Methyl 2-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Altenbach, Robert J.; Black, Lawrence A.; Chang, Sou-Jen; Cowart, Marlon D.; Faghih, Ramin; Gfesser, Gregory A.; Ku, Yi-yin; Liu, Huaqing; Lukin, Kirill A.; Nersesian, Diana L.; Pu, Yu-ming; Sharma, Padam N.; Bennani, Youssef L.; US2004/92521; (2004); 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. 4387-36-4, name is 2-Iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H4IN

2-iodobenzonitrile (1.5mmol) was dissolved in a 3:2 mixture of Net3/THF (10 mL) and degassed for 30 min at room temperature. After adding of PdCl2(PPh3)2 (0.2 mol %) and CuI (0.2mol %), alkyne (1.8mmol) was added dropwise to the reaction suspension. Subsequently the reaction mixture was stirred at room temperature until completion was indicated by TLC. After the completion of the reaction, the reaction mixture was filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography (petroleum ether : ethyl acetate = 30:1) to provide 1a (yield: 78%), 1k-1s (in 77-85% yield).

According to the analysis of related databases, 4387-36-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 6828-35-9, These common heterocyclic compound, 6828-35-9, name is 5-Chloro-2-iodoaniline, 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 solution of 2-iodoaniline (0.5 mmol) and benzaldehyde (0.6mmol) in dry DMSO (1.5 mL), selenium powder (1.5 mmol), catalyst(0.05 mmol), and KOH (1.0 mmol) were added, the reactionmixture was stirred in a sealed tube under argon atmosphere at 120 C for 36 h. After the reaction was finished,the mixture was cooled to r.t., diluted with sat. aq NH4Cl (15mL), and extracted with EtOAc (3 × 10 mL). The organic layerwas dried over Na2SO4, and the solvent was removed underreduced pressure. The residue was purified by silica gel columnchromatography to afford the corresponding product 3aa.

Statistics shows that 5-Chloro-2-iodoaniline is playing an increasingly important role. we look forward to future research findings about 6828-35-9.

Reference:
Article; Su, Tao; Xie, Shishun; Li, Bifu; Yan, Jun; Huang, Ling; Li, Xingshu; Synlett; vol. 26; 2; (2015); p. 215 – 220;,
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. 34270-90-1, name is 1-Iodo-2-(2-iodoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Iodo-2-(2-iodoethoxy)ethane

A N,N-dimethylformamide (0.5 mL) solution of (ls,4s)-4-(4-(2-((2,6- difluorobenzyl)oxy)- 1,1,1 ,3 ,3 ,3 -hexafluoropropan-2-yl)phenyl)-4-((4- fluorophenyl)sulfonyl)cyclohexanamine (10 mg, 0.016 mmol), l-iodo-2-(2- iodoethoxy)ethane (15.63 mg, 0.048 mmol) and potassium carbonate (26 mg, 0.188 mmol) was stirred at room temperature for 3 days. LCMS analysis showed that the reaction was near completion. The mixture was diluted with ethanol (1 mL) and filtered. The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge CI 8, 19 x 250 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 40-100% B over 25 minutes, then a 5- minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give Example 8 (4.5 mg, 36% yield). LC/MS (M+l): 696.3; LC retention time: 2.46 min (analytical HPLC Method B); 1H NMR (400 MHz, 1 : 1 mixture of CDC13-CD30D) delta ppm 7.60 (d, J=8.4 Hz, 2H), 7.43 – 7.34 (m, 3H), 7.24 (dd, J=8.9, 5.1 Hz, 2H), 7.02 – 6.90 (m, 4H), 4.73 (s, 2H), 3.79 (br. s., 3H), 2.81 (d, J=8.1 Hz, 2H), 2.51 (br. s., 3H), 2.28 – 2.06 (m, 5H), 1.46 – 1.20 (m, 4H).

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 34270-90-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUAN, Jingwu; DHAR, T. G. Murali; JIANG, Bin; KARMAKAR, Ananta; GUPTA, Arun Kumar; LU, Zhonghui; WEIGELT, Carolyn A.; WO2015/103507; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 628-77-3, name is 1,5-Diiodopentane, 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 628-77-3, Product Details of 628-77-3

(S) – (4-hydroxy-5-methoxy-2-nitrophenyl) (2- (hydroxymethyl) -4-methylenepyrrolidin-1-yl) methanone (0.801 g, 2.60 mmol) in butanone (10 ml) was added Cs 2CO 3, (2.50 g, 7.67 mmol) , followed by addition of 1, 5-diiodopentane (415 mmol, 1.28 mmol) . The mixture was stirred for 26 h, concentrated and purified on SiO 2 column eluted with MeOH/CH 2Cl 2 (1: 15 to 1: 5) to afford the title compound (0.675 g, 77%yield, 95%pure) . MS ESI m/z calcd for C 33H 41N 4O 12 [M+H] + 685.26, found 685.60.

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

Reference:
Patent; HANGZHOU DAC BIOTECH CO., LTD; ZHAO, Robert Yongxin; ZHUO, Xiaotao; YANG, Qingliang; ZHAO, Linyao; HUANG, Yuanyuan; YE, Hangbo; YANG, Chengyu; LEI, Jun; GAI, Shun; GUO, Huihui; JIA, Junxiang; BAI, Lu; XIE, Hongsheng; ZHOU, Xiaomai; GUO, Zhixiang; LI, Wenjun; CAO, Mingjun; ZHENG, Jun; YE, Zhichang; YANG, Yanlei; (325 pag.)WO2020/6722; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com