Tag: M.W=200-300

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

These common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, 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. Product Details of 103440-52-4

General procedure: A dry, N2 flushed 25 mL round-bottomed flask, equipped with a magnetic stirring bar, was charged with aryl iodide 3 (1 mmol) in anhydrous THF (5 mL), and cooled to -40 C. i-PrMgCl (2 M in THF, 2 mmol) was slowly added. After 0.5 h, CuCN¡¤2LiCl (premixed CuCN and 1 M LiCl in THF) (0.1 mmol) was added. After 5 min, at the same temperature, 2-chloro-3-iodo-propene (2 mmol) was added and the reaction mixture allowed to warm to rt. The reaction mixture was quenched with sat. NH4Cl (20 mL) and extracted with MTBE (2 ¡Á 20 mL). The combined organic fractions were washed with brine (10 mL), then dried over Na2SO4, and concentrated in vacuo. The crude product was used in the next step after a silica plug treatment or without further purification.

The synthetic route of Methyl 2-Iodo-5-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Linghu, Xin; McLaughlin, Mark; Chen, Cheng-Yi; Reamer, Robert A.; Dimichele, Lisa; Davies, Ian W.; Tetrahedron Letters; vol. 53; 13; (2012); p. 1550 – 1552;,
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. 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, A new synthetic method of this compound is introduced below., Quality Control of 3-Iodo-4-methylbenzoic acid

To a stirring solution of 3-iodo-4-methylbenzoic acid (60 g, 0.22 mol, 1 eq) in degassed DMF (1400 niL, 23.3 vol.) was charged 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-l,3,2- dioxaborolane (81.4 g, 0.32 mol, 1.4 eq) followed by potassium acetate (112 g, 1.14 mole, 5eq) and [1,1 ‘-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (18.7 g, 0.02 mole, 0. leq). The resulting mixture was placed under a nitrogen atmosphere and was heated to 80 0C with the exclusion of light overnight. The mixture was then concentrated under high vacuum and the residue partitioned between EtOAc and 2M HCl. The mixture was then filtered and the layers separated. The aqueous phase was re-extracted with EtOAc. The combined organics were then washed with brine, dried and evaporated to yield a brown solid that was applied to a silica plug then eluted with 2:1 cyclohexane : ethyl acetate. Fractions were then combined and evaporated to yield a brown foam that was triturated with cyclohexane, collected by filtration then dried in vacuo to yield 4-methyl-3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)benzoic acid, delta (CDCl3) 8.50-8.49 (IH, d), 8.04-8.02 (IH, dd), 7.27-7.25 (IH, d), 2.61 (3H, s), 1.36 (12H, s).

The synthetic route of 82998-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/147104; (2007); A2;,
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. 68507-19-7, name is 3-Iodo-4-methoxybenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H7IO3

[00164] To 26.9 mg PdCl2(dppf).CH2Cl2 in a reaction tube under nitrogen were added 4 ml dioxane, 0.43 ml (3 mmol) triethylamine, 0.35 ml (2.4 mmol) pinacolborane and 277 mg (1.0 mmol) 3-iodo-4-methoxybenzoic acid. The reaction solution was stirred at room temp. to ensure that all the phenolic groups had reacted with pinacolborane and the hydrogen evolved was flushed out of the reaction tube with argon. The reaction solution was warmed to 80 C. with stirring in an oil bath for 8 h. An aliquot (0.3 ml) was removed from the reaction solution, extracted into ethyl acetate, washed with dilute sulphuric acid and then several times with water and analysed by gc (fid detector, SGE HT5 capillary column). There was only one peak in the gc at retention time longer than that for 3-iodo-4-methoxybenzoic acid and that was confirmed by gc/ms to be due to the desired arylboronic acid pinacol ester.

According to the analysis of related databases, 68507-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 13194-68-8,Some common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, 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.

Preparation 1 5-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid To a stirred solution comprised of 1.88 g (0.00791 mol) of 2-amino-5-iodotoluene in 10 mL of tetrahydrofuran at -78 C. was added 6 mL (0.012 mol) of a 2.0 M lithium diisopropylamide in tetrahydrofuran/heptane/ethylbenzene (Aldrich) solution. The resulting green suspension was stirred vigorously for 10 minutes, after which time a solution of 1.00 g (0.00392 mol) of 5-bromo-2,3,4-trifluorobenzoic acid in 15 mL of tetrahydrofuran was added. The cold bath was subsequently removed, and the reaction mixture stirred for 18 hours. The mixture was concentrated, and the concentrate was treated with 100 mL of dilute (10%) aqueous hydrochloric acid. The resulting suspension was extracted with ether (2*150 mL), and the combined organic extractions were dried (MgSO4) and concentrated in vacuo to give an orange solid. The solid was triturated with boiling dichloromethane, cooled to ambient temperature, and collected by filtration. The solid was rinsed with dichloromethane, and dried in the vacuum-oven (80 C.) to afford 1.39 g (76%) of a yellow-green powder; mp 259.5-262 C.; 1H NMR (400 MD, DMSO): delta9.03 (s, 1H), 7.99 (dd, 1H, J=7.5, 1.9 Hz), 7.57 (dd, 1H, J=1.5 Hz), 7.42 (dd, 1H, J=8.4, 1.9 Hz), 6.70 (dd, 1H, J=8.4, 6.0 Hz), 2.24 (s, 3H); 19F NMR (376 MHz, DMSO): delta-123.40 to -123.47 (m); -139.00 to -139.14 (m); IR (KBr) 1667 (C=O stretch)cm-1; MS (CI) M+1=469. Anal. Calcd/found for C14H9BrF2INO2: C, 35.93/36.15; H. 1.94/1.91; N, 2.99/2.70; Br, 17.07/16.40; F, 8.12/8.46; I, 27.11/26.05.

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

Reference:
Patent; Barrett, Stephen Douglas; Biwersi, Cathlin Marie; Chen, Michael Huai Gu; Kaufman, Michael David; Tecle, Haile; Warmus, Joseph Scott; US2004/54172; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 3032-81-3, name is 1,3-Dichloro-5-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. Formula: C6H3Cl2I

General procedure: To a solution of phenol 3 (0.45 mmol), aryl iodide 2 (0.45 mmol), ferrocenyl allene 1 (0.3 mmol) and Cs2CO3 (0.9 mmol) in MeCN (2.0 mL)was added Pd(PPh3)4 (0.015 mmol) under a N2 atmosphere. The resulting mixture was heated at 80 ¡ãC for 2 h. After completion of thereaction, the mixture was cooled to room temperature. The solvent was removed under vacuum, and the resulting residue was purified on a silica gel column (PE/EtOAc, 10:1) to provide the corresponding ferrocene-containing allylic ester product

The synthetic route of 1,3-Dichloro-5-iodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Xin-Xing; Wang, Chenjun; Zhao, Wanrong; Zhao, Haiying; Chen, Shufeng; Synthesis; vol. 50; 20; (2018); p. 4097 – 4103;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 3930-83-4, These common heterocyclic compound, 3930-83-4, name is 2-Iodobenzamide, 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: A two-neck round bottom flask was charged with amagnetic stirrer, evacuated and backfilled with argon. 2-iodobenzamide ( 0.5mmol, 124 mg), aniline or alpha-substituted benzylamine (1.0 mmol), K2CO3(1.0 mmol, 138 mg) and CuBr2 (0.05mmol, 11 mg) in DMSO (5 mL) under argon atmosphere. The mixture was allowed tostir under argon atmosphere at 110 C for 4 h.The mixture was concentrated with the aid of a rotary evaporator, and theresidue was purified by column chromatography on silica gel using petroleumether/ethyl acetate (2:1) as eluent to provide the product 2-9.

Statistics shows that 2-Iodobenzamide is playing an increasingly important role. we look forward to future research findings about 3930-83-4.

Reference:
Article; Wang, Li-Xia; Hu, Ben-Quan; Xiang, Jun-Feng; Cui, Jie; Hao, Xiang; Liang, Tong-Ling; Tang, Ya-Lin; Tetrahedron; vol. 70; 45; (2014); p. 8588 – 8591;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 202865-85-8, These common heterocyclic compound, 202865-85-8, name is 1-Bromo-4-iodo-2-methylbenzene, 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.

To a solution of compound LXXXVI-1 (1.5 g, 4.9 mmol) in DME:H20 = 3: 1 (20 mL), Na2C03 (1.05 g, 9.9mmol) and compound LXXXVI-1A (1.47 mg, 4.9 mmol) were added, the resulting mixture was purged with nitrogen, then Pd (dppf)Cl2 (182 mg, 0.2 mmol) was added. The reaction mixture was stirred at 80 C overnight under nitrogen protection. After completion of the reaction, the mixture was poured into water, extract with EtOAc (30 mL x 3), the combined organic layers were dried over Na2S04, concentrated in vacuo. The residue was purified by chromatography (PE:EA = 100: 1) to afford compound LXXXVI-2 (1.06 g , yield 59.6%).

Statistics shows that 1-Bromo-4-iodo-2-methylbenzene is playing an increasingly important role. we look forward to future research findings about 202865-85-8.

Reference:
Patent; INTERMUNE, INC.; BUCKMAN, Brad, O.; NICHOLAS, John, B.; EMAYAN, Kumaraswamy; SEIWERT, Scott, D.; WO2013/25733; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com