Category: iodides-buliding-blocks

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 1258298-01-9 as follows. Recommanded Product: 2,6-Dichloro-4-iodobenzoic acid

Thionyl chloride (20 mL) was added to 2,6-dichloro-4-iodobenzoic acid (1.5 g, 4.73 mmol) and the mixture was heated to reflux for 5 h under nitrogen. After cooling the mixture was concentrated under reduced pressue. Toluene (10 mL) was added and the mixture was concentrated under reduced pressure again to remove residual thionyl chloride. The residue was dissolved in anhydrous THF (20 mL) and this was added dropwise to a cooled (0 C.) solution of 4-aminopyridine (0.53 g, 5.68 mmol) and triethylamine (1.32 mL, 9.46 mmol) in anhydrous THF (20 mL). After addition was complete, the mixture was stirred at room temperature under nitrogen overnight. The reaction was poured onto the ice water (50 mL) and extracted with EtOAc (2¡Á50 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hexanes/EtOAc=3:1) to afford the desired product (1.8 g, yield: 97%.) 1HNMR (DMSO-d6, 400 MHz): 611.14 (s, 1H), 8.47 (dd, J=1.6, 4.8 Hz, 2H), 8.03 (d, J=2.0 Hz, 2H), 7.59 (dd, J=1.6, 4.8 Hz, 2H). LCMS (ESI) m/z: 393.0 [M+H+].

According to the analysis of related databases, 1258298-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; US2010/317643; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 101066-87-9, 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 101066-87-9 as follows.

Reference Example 88 4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-ethyl-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile A suspension of (4S,5S)-4-(tert-butyldimethylsilyloxy)-5-ethylpyrrolidin-2-one (6.00 g), 4-iodo-2-trifluoromethylbenzonitrile (8.42 g), cesium carbonate (12.05 g), tris(dibenzylideneacetone)dipalladium(0) (1.13 g) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (2.14 g) in toluene (70 mL) was stirred at 80 C. for 18 hr. Water and ethyl acetate were added to the reaction mixture and insuluble material was filtered off. The filtrate was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1?1/2) to give the title compound as a pale-yellow solid (yield: 7.76 g, 76%). 1H-NMR(CDCl3)delta:0.14(3H,s), 0.14(3H,s), 0.93(9H,s), 0.96(3H,t,J=7.5 Hz), 1.60-1.78(1H,m), 1.77-1.94(1H,m), 2.66(1H,dd,J=17.0,6.8 Hz), 2.76(1H,dd,J=17.0,7.2 Hz), 4.16-4.26(1H,m), 4.66(1H,q,J=6.9 Hz), 7.81-7.87(2H,m), 7.94-7.99(1H,m).

According to the analysis of related databases, 101066-87-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2009/42967; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 755027-18-0, 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. 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of l-bromo-4-iodo-2-methoxybenzene (L. A. Hasvold et al, US 2004/0254159, EXAMPLE 57B) (33.45 g, 107 mmol) in MeCN (100 mL) was added acrylic acid (9.61 g,, 133 mmol), Et3N (37.2 mL, 267 mmol) and palladium acetate (719 mg, 3.2 mmol). The reaction mixture was heated to 9O0C for 40 minutes, cooled to RT and poured into 2.4 L IM HCl. After stirring for 30 minutes, the solid was filtered, heated to reflux in EtOH (230 mL), allowed to cool to RT and stirred overnight. The solid was filtered and washed with 1 : 1 EtOH hexane (50 mL) to give desired product. LRMS ESI+ (M+H)+ 257.0.

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

Reference:
Patent; MERCK & CO., INC.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2008/51475; (2008); A2;,
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. 618-91-7, name is Methyl 3-iodobenzoate, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

General procedure: A 50 mL round-bottomed flask, equipped with a gas inlet tube, a refluxcondenser and a magnetic stirring bar was charged with MCM-41-2PPdCl2 (102 mg, 0.05 mmol Pd), aryl halide (5.0 mmol) and HCOONa(7.5 mmol). The flask was flushed with CO. DMF (5 mL) was addedby syringe and a slow stream of CO was passed into the suspension.The mixture was vigorously stirred at 110-130 C for 2-20 h, cooledto room temperature and diluted with diethyl ether (50 mL). Thepalladium catalyst was separated from the mixture by filtration,washed with distilled water (2 ¡Á 10 mL), ethanol (2 ¡Á 10 mL) and ether(2 ¡Á 10 mL) and reused in the next run. The ethereal solution waswashed with water (3 ¡Á 20 mL), and dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by flash column chromatography on silica gel (hexane-ethylacetate = 10 : 1).

The synthetic route of 618-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jiang, Jianwen; Wang, Pingping; Cai, Mingzhong; Journal of Chemical Research; vol. 38; 4; (2014); p. 218 – 222;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 89459-38-1, name is 2-Iodo-4-nitrobenzoic acid, 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. COA of Formula: C7H4INO4

[0168] Oxalyl chloride (12 ml, 17.3 g, 0.14 mol) was added dropwise to a solution of 2-iodo-4-nitrobenzoic acid I-1 b (20 g, 68.3 mmol) in dichloromethane (137 ml). N,N-Dimethylformamide (0.1 ml) was added to the reaction mixture via syringe, the reaction mixture was stirred at 23 C. for 1 hour, and another portion of N,N-dimethylformamide (0.1 ml) was added. After stirring the reaction mixture another 2 hours, the reaction mixture was concentrated in vacuo. The residue was taken up in dichloromethane (137 ml), and DMAP (50 mg) and triethylamine (14.3 ml, 10.3 g, 0.102 mol) were added. The mixture was cooled to 0 C. and N-ethylaniline (10.1 ml, 9.9 g, 82 mmol) was added over a 10 min period. The reaction mixture was warmed to 23 C. After 16 hours at this temperature, water (150 ml) was added, and the layers were separated. The organics were washed with 1 N HCl (2 100-ml portions), dried over anhydrous sodium sulfate, and were concentrated. Purification of the residue by flash column chromatography (dichloromethane) afforded N-ethyl-2-iodo-4-nitro-N-phenyl-benzamide I-1gamma (24.3 g, 93%).

The synthetic route of 2-Iodo-4-nitrobenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2004/122038; (2004); 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. 25245-27-6, name is 1-Iodo-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Iodo-3,5-dimethoxybenzene

1. Condensation reaction: in with a thermometer, condenser 250 ml four bottle is added between the 26.7g 5 – iodo – teredimethyl ether, 12.8g bromopropylene, 20.4g triethylamine, 2.2g dppp nickel chloride, 130 ml methyl tert-butyl ether, magnetic stirring, oil bath heating, when the temperature rises to 80 C and maintaining at 4 hours, after the reaction is cooled to ambient temperature, for 60 ml 10% hydrochloric acid aqueous solution washing the reaction liquid, water washed to neutral, the organic layer is distilled under reduced pressure to obtain between the 21.4g 5 – propenyl – teredimethyl ether, yield 96.1%.

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; Weifang Xian Da Chemical Co., Ltd.; Li Kai; Wang Guangyue; Yang Qiwei; Zou Yabo; (7 pag.)CN106748673; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 6940-76-7, name is 1-Chloro-3-iodopropane, molecular formula is C3H6ClI, 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. Recommanded Product: 1-Chloro-3-iodopropane

Lithium diisopropylamide in THF (2.0 M; 12 mL, 24 mmol) was added to a mixture of 2-fluoro-3-iodopyridine (Alfa Aesar, 5.0 g, 22 mmol) in THF (50 mL) at -78 C. The solution was stirred at -78 C. for 1 h, then a solution of 1-chloro-3-iodo-propane, (5.0 g, 24 mmol) in 15 mL THF was added dropwise. The reaction mixture was stirred at -78 C. for 30 min., then allowed to warm to room temperature. The reaction mixture was quenched with aq.NH4Cl and extracted with EtOAc. The combined organic extract was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using CombiFlash apparatus, eluting with 0 to 50% EtOAc/hexanes, to give the sub-title compound (6.2 g, 92%). LCMS calc. for C8H9ClFIN (M+H)+: m/z=299.9. Found: 300.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6940-76-7, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; Xue, Chu-Biao; Li, Yun-Long; Geng, Hao; Pan, Jun; Wang, Anlai; Zhang, Ke; Yao, Wenqing; Zhang, Fenglei; Zhuo, Jincong; US2014/200227; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, 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 5471-81-8, name: Methyl 4-iodo-3-methylbenzoate

General procedure: In Scheme VIII, the bromobenzyldiazepan XXXIV is coupled with a substituted iodobenzoate ester XXXVIII (from Scheme VII) in the presence of diboron pinacol ester (B2pin2) to form the biphenyl ester XLI with substitution in both phenyl rings.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-iodo-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; ZECH, Stephan, G.; KOHLMANN, Anna; LI, Feng; WANG, Yihan; ZHOU, Tianjun; DALGARNO, David, C.; SHAKESPEARE, William, C.; ZHU, Xiaotian; WO2014/151761; (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. 23399-70-4, name is 5-Chloro-2-iodotoluene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H6ClI

Intermediate 6: 2:1 Mixture of 2-(bromomethyl)-4-chloro-1-iodobenzene and 1- bromo-2-(bromomethyl)-4-chlorobenzene; Lambda/-bromosuccinimide (6.34 g, 35.6 mmol) was weighed into a flask and carbon tetrachloride (200 ml) was added followed by 4-chloro-1-iodo-2-methylbenzene (8.57 g, 33.9 mmol, Fluorochem Ltd). The reaction mixture was stirred and dibenzoyl peroxide (0.822 g, 3.39 mmol) was added in one portion. The apparatus was then flushed three times with nitrogen and heated to reflux with vigorous stirring. After approximately 46 h at reflux, the reaction was allowed to cool to room temperature. The reaction mixture was filtered to remove the insoluble material and washed with aqueous sodium sulfite solution. The carbon tetrachloride layer was dried over sodium sulfate and evaporated to give a crude product as a pale yellow oil which crystallised on standing. The crude product was triturated with cyclohexane. The white insoluble material (1.30 g) was retained. The soluble material was then loaded onto 50 g silica SPE (pre-conditioned with cyclohexane) and was eluted with cyclohexane. Two product batches were obtained from this purification. The slower running material was obtained as a clear liquid which crystallised on standing to give the title compounds as a 2:1 mixture of 2- (bromomethyl)-4-chloro-1-iodobenzene and 1-bromo-2-(bromomethyl)-4- chlorobenzene (1.99 g).The faster running material (2.07 g) was combined with the triturated material (1.30 g) and was re-purified on 50 g silica SPE eluting with cyclohexane, exactly as before. A second batch of the title compounds, again as a 2:1 of 2-(bromomethyl)-4-chloro-1- iodobenzene and 1-bromo-2-(bromomethyl)-4-chlorobenzene (2.38 g) was obtained; LCMS: (System 2) tRET = 1 -37 min (no ions detected).; Intermediate 7: 1 -r(5-Chloro-2-iodophenyl)methyl1-Lambda/-(2,6-difluorophenyl)-1 H- pyrazole-3-carboxamide/V-(2,6-difluorophenyl)-1 H-pyrazole-3-carboxamide (350 mg, 1.57 mmol), 2:1 Mixture of 2-(bromomethyl)-4-chloro-1-iodobenzene and 1-bromo-2-(bromomethyl)-4- chlorobenzene (495 mg, 1.57 mmol) and potassium carbonate (433 mg, 3.14 mmol) were weighed into a flask. DMF (15 ml) was then added and the reaction was stirred at ambient temperature under nitrogen.After 16 h, the reaction mixture was partitioned between DCM (100 ml) and water (100 ml). The layers were separated and the aqueous layer extracted with further DCM (50 ml). The combined DCM extracts were dried (sodium sulfate) and evaporated to give a crude product as an oil. This product was re-dissolved in DCM and loaded on to 50 g silica SPE which had been pre-equilibrated with cyclohexane. The product was then purified using 0-50% ethyl acetate-cyclohexane gradient to give a white solid (2:1 mixture of iodide and bromide).200 mg of the product mixture was purified by MDAP (2 x 100 mg batches). Each sample was dissolved in 1 :1 MeOH:DMSO (1 ml) and purified (supelcosil ABZ+Plus column) (Method A) eluting with solvents A/B (A: Water + 0.1% Formic acid, B: MeCN:Water 95:5 + 0.05% Formic acid).The first eluted product from each run was combined and partitioned between NaHCO3 (aq) and DCM. The layers were separated and the aqueous layer was extracted with a second portion of DCM. The DCM extract was dried (Na2SO4) and evaporated to give 1-[(2-bromo-5-chlorophenyl)methyl]-Lambda/-(2,6-difluorophenyl)-1 H- pyrazole-3-carboxamide as a colourless oil, 45 mg; LCMS: (System 2) MH+= 426, 428 and 430 (Cl, Br isotopes), tRET = 1.22 min.The second eluted product from each run was combined and partitioned betweenNaHCO3 (aq) and DCM. The layers were separated and the aqueous layer was extracted with a second portion of DCM. The DCM extract was dried (Na2SO4) and evaporated to give the title compound as a colourless oil (121 mg); LCMS: (System2) MH+= 474 and 476 (Cl isotopes) tRET = 1 -25 min.

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 23399-70-4.

Reference:
Patent; GLAXO GROUP LIMITED; COE, Diane, Mary; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; SENGER, Stefan; VILE, Sadie; WO2010/122088; (2010); 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. 5460-32-2, name is 4-Iodo-1,2-dimethoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H9IO2

General procedure: The appropriate 2-amino-5H-benzothiopyrano[4,3-d]pyrimidine 22a-c (0.417mmol) was added, at room temperature, under nitrogen atmosphere, to 0.079g of CuI (0.417mmol) and 0.115g of anhydrous K2CO3 (0.833mmol). Then, the appropriate substituted aryl iodide (0.694mmol), 0.04mL of DMEDA (0.417mmol) and 2.5mL of dioxane were added. The reaction mixture was heated at 100¡ãC and allowed to stir for 24h. After cooling, the reaction mixture was added with 2.5mL of concentrated NH3 and with a saturated solution of NaCl (10-15mL). The mixture was extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated under reduced pressure giving a residue which was purified by flash chromatography using petroleum ether 60-80¡ãC/ethyl acetate 5:5 as the eluting system, to give compounds 1-21. 4.1.1.20 8-Chloro-2-(3,4-dimethoxyanilino)-5H-benzothiopyrano[4,3-d]pyrimidine (20) Yield: 35percent; m. p. 180-183?¡ãC; 1H NMR (400?MHz, DMSO-d6): delta 3.75 (s, 3H), 3.78 (s, 3H), 4.04 (s, 2H), 6.90 (d, J?=?8.8?Hz, 1H), 7.23 (dd, Jmin?=?2.2?Hz, Jmax?=?9.0?Hz, 1H), 7.44 (dd, Jmin?=?1.8?Hz, Jmax?=?8.6?Hz, 1H), 7.55-7.60 (m, 2H), 8.27 (d, J?=?8.4?Hz, 1H), 8.44 (s, 1H), 9.53 (s, 1H) ppm; 13C NMR (100?MHz, DMSO-d6): delta 25.92, 55.32, 55.85, 104.33, 110.64, 112.35, 114.18, 122.31, 126.20, 127.16, 128.42, 131.02, 134.18, 135.65, 138.86, 143.69, 148.54, 156.71, 159.41?ppm; HRMS (ESI) m/z calculated for C19H17ClN3O2S ([M+H]+) 386.07300, found 386.07244. Anal. C19H16ClN3O2S (C, H, N).

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:
Article; Salerno, Silvia; Garcia-Argaez, Aida Nelly; Barresi, Elisabetta; Taliani, Sabrina; Simorini, Francesca; La Motta, Concettina; Amendola, Giorgio; Tomassi, Stefano; Cosconati, Sandro; Novellino, Ettore; Da Settimo, Federico; Marini, Anna Maria; Via, Lisa Dalla; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 446 – 456;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com