Tag: M.W=200-300

Reference of 3032-81-3, A common heterocyclic compound, 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, molecular formula is C6H3Cl2I, 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.

Preparation of 1,3-dichloro-5-iodo-2-methylbenzene To the mixture of LDA (5 mL, 8.6 mmol) in THF (20 mL) was added compound 1,3-dichloro-5-iodobenzene (2.35 g, 8.6 mmol) under -78° C. Then the mixture was added to the pre-cooled solution of (CH3)2SO4 (12 mL, 10.3 mmol) in THF (10 mL) under -78° C. The solution was concentrated under vacuum. The residue was diluted with EA, washed with 1N HCl, 1N NaOH, brine, dried over Na2SO4, concentrated under vacuum to give the desired product (2.3 g, 93percent yield).

The synthetic route of 3032-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; Akama, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131016; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 89459-38-1, name is 2-Iodo-4-nitrobenzoic acid, 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 89459-38-1, Application In Synthesis of 2-Iodo-4-nitrobenzoic acid

Step 4: A’-{3-(2-{IM]u0r0met oxy)phenyl)-4,4-d^ A flask was charged with 2-iodo-4-mtrobenzoic acid (i .0 g, 3.41 mmol) in DCM (25 ml,), oxalyl chloride (0.597 mL, 6.83 mmol) and a drop of DMF. After about 20 min the mixture was concentrated under reduced pressure, dissolved in DCM (25 mL) then added to the crude 3-(2-(difluoromethoxy)phenyl)-4,4- dimethoxybutan-1 -amine (3.15 g from step 3, assumed 3.41 mmol) in DCM (25 mL) with TEA (5 mL, 35.9 mmol). The mixture was stirred for about 15 min at rt then water (50 ml.) was added and stirring continued for about 5 min. The solvent layers were separated then the aqueous layer was extracted with DCM (20 mL). The combined organics were washed with saturated sodium bicarbonate (2 x 20 mL) then dried over MgS04, filtered and concentrated under reduced pressure. The material was purified via flash chromatography on silica gel (0-25% EtOAc/DCM). The appropriate fractions were collected and concentrated under reduced pressure to give the title compound (1.23 g, 66%); LC/MS (Table A, Method b) R, – 2.37 min; MS m/z 549 (M-H)”

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ABBVIE INC.; BREINLINGER, Eric; BURCHAT, Andrew; DIETRICH, Justin; FRIEDMAN, Michael; IHLE, David; KINSMAN, David; MULLEN, Kelly; OSUMA, Augustine; VASUDEVAN, Anil; WILSON, Noel, S.; (101 pag.)WO2016/168638; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 58313-23-8,Some common heterocyclic compound, 58313-23-8, name is Ethyl-3-iodobenzoate, molecular formula is C9H9IO2, 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.

6-(Methyloxy)-3,4-dihydro-l(2H)-isoquinolinone (0.319 g, 1.8 mmol), ethyl-3- iodobenzoate (0.62 niL, 3.68 mmol), copper (I) iodide (0.044g, 0.23 mmol), potassium carbonate (0.247 g, 1.8 mmol) and lambda/,N-dimethylformamide (4 mL) were combined and the stirred reaction mixture was heated at 150 0C under nitrogen for 28 h. The reaction mixture was partitioned between water and ethyl acetate. The layers were separated and the aqueous phase was extracted with ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give a gold-yellow liquid. The crude product was purified by flash chromatography over silica with a hexanes:ethyl acetate gradient (100:0 to 50:50) to give 0.32 g (55%) of ethyl 3-[6-(methyloxy)-l-oxo-3,4-dihydro-2(lH)- isoquinolinyl]benzoate as a clear colorless oil. 1H NMR (400 MHz; CDCl3): delta 8.10 (d, J = 9 Hz, IH), 8.00 (s, IH), 7.91 (d, J = 8 Hz, IH), 7.63 (d, J = 8 Hz, IH), 7.46 (t, J = 8 Hz, IH), 6.89 (dd, J = 9, 2 Hz, IH), 6.73 (d, J = 2 Hz, IH), 4.38 (q, J = 7 Hz, 2H), 4.01 (t, J = 6 Hz, 2H), 3.87 (s, 3H), 3.12 (t, J = 6 Hz, 2H), 1.38 (t, J = 7 Hz, 3H). ES- LCMS m/z 326(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 Ethyl-3-iodobenzoate, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/5998; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 21304-38-1, 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. 21304-38-1 name is 4-Iodobenzene-1,2-diamine, 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.

4-Iodo-benzene-l,2-diamine was prepared by the literature procedure The diamine was reacted with hexaketocyclohexane octahydrate to give [(HATNA)I3]. The compound is a green colored solid. It is slightly soluble in a mixture of chloroform/TFA.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodobenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; WO2005/123737; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 627-31-6, 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. 627-31-6 name is 1,3-Diiodopropane(stabilized with Copper chip), 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 19Synthesis of: 4-((/?)-2-amino-3-((/?)-2,3-bis(dodecanoyloxy)propylthio)propanamido)-l,l- difluorobutylphosphonic acidStep 1: diethyl 1 ,1 -difluoro-4-iodobut lphosphonate[000492] To a solution of diisopropylamine (1.6 eq) in THF (1.28 M) was slowly added n- butyllithium (1.5 M in cyclohexane, 1.5 eq) dropwise at 0 C. The reaction mixture was stirred at 0 C for 40 minutes. The mixture was then cooled down to -78 C, and diethyldifluoromethylphosphonate (1 eq) in HMPA (2.1 M) was slowly added to the reaction. Then the mixture was stirred at -78 C for 40 minutes and to the resulting solution was added a cooled solution of 1,3-diiodopropane (12.8 M in THF, 4 eq) rapidly. After 1.5 hours, the reaction was quenched by pouring into saturated NH4C1 solution. The aqueous phase was extracted with ethyl acetate three times. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate and concentrated en vaccuo. The resulting crude was purified by flashchromatography on a COMBIFLASH system (ISCO) using 10-100% EtOAc/Hex to give the product as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Diiodopropane(stabilized with Copper chip), and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; WU, Tom Yao-Hsiang; ZOU, Yefen; HOFFMAN, Timothy Z.; PAN, Jianfeng; WO2011/119759; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, molecular formula is C7H4F3I, 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. Safety of 1-Iodo-3-(trifluoromethyl)benzene

The mixture of Intermediate-51a (150mg, 0.45mmol), l-iodo-3(trifluoromethyl)benzene (0.18g,0.68 mmol) and CS2CO3 (0.22 g, 0.68 mmol) in toluene (7mL) was degassed for 15 min by purging nitrogen followed by addition of bis (tri-tert-butylphosphine palladium(O) (11.53mg, 0.023 mmol) and tris dibenzylidene acetone dipalladium (0)(20.66mg,0.023 mmol). The reaction mixture was heated to 110C and further maintained for 20 hr at the same temperature. The reaction mixture was cooled to room temperature and progress of reaction monitored by TLC. The mixture was diluted with ethyl acetate, filtered through celite and concentrated under vacuum to give crude compound. This crude compound was further purified by flash chromatography using a mixture of 20% ethylacetate in hexane (0.17g, 79%).Ethereal HCl (2 mL) was added and stirred for 10 min. The solvent was evaporated and solid washed by diethyl ether (2 mL) followed by «-pentane (2 ml), dried to get HCl salt of title compound.m/z 477.2; *H NMR (400 MHz, DMSO-d6): delta 9.64 (bs, IH), 9.10 (bs, IH), 8.24 (d, 7=8.4 Hz, IH), 8.03 (t, 7=8.8 Hz, 2H), 7.89 (d, 7=7.2 Hz, IH), 7.63-7.48 (m, 6H), 7.37(d, 7=7.6 Hz, IH), 6.93 (d, 7=7.2 Hz, IH), 6.80-6.77 (m, 3H), 5.34 (m, lH), 4.28 (m, 1H),3.85 (m, lH), 3.47-3.10 (m, 3H), 2.03 (m, 2H), 1.67 (d, 7=6.8 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 401-81-0, its application will become more common.

Reference:
Patent; LUPIN LIMITED; SHUKLA, Manojkumar, Ramprasad; ANKUSH, Sarde, Gangaram; VIPUL, Pachpute, Dilip; KULKARNI, Sanjeev, Anant; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2012/127385; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

3032-81-3, name is 1,3-Dichloro-5-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: 1,3-Dichloro-5-iodobenzene

General procedure: A suspension of coupling substrate 2d?g (1 equiv), copper(I) iodide (0.5 equiv), cesium carbonate (2 equiv), and the corresponding aryl halide (1 equiv) in dioxane was placed under a nitrogen atmosphere. The coupling ligand DMEDA (1 equiv) was added dropwise by using a syringe and the mixture was then stirred at r.t. for various periods of time (2.5?48 h). At the end of the reaction, all insoluble salts deposited after cooling at r.t. were collected by filtration then washed with dichloromethane. The resulting filtrate was concentrated in vacuo and the residue was partitioned between water and dichloromethane. The organic layer was dried over MgSO4 and evaporated to dryness. The reaction residues were recrystallized or purified by chromatography on silica gel column to afford pure compounds 36?39.

The synthetic route of 3032-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baudelet, Davy; Daich, Adam; Rigo, Benoit; Lipka, Emmanuelle; Gautret, Philippe; Homerin, Germain; Claverie, Christelle; Rousseau, Jolanta; Abuhaie, Cristina-Maria; Ghinet, Alina; Synthesis; vol. 48; 14; (2016); p. 2226 – 2244;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 128140-82-9, 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. 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step a) 3-((4-(Difluoromethoxy)phenyl)ethynyl)phenol A solution of 4-(difluoromethoxy)phenyl iodide (4.70 g) in deoxygenated dimethylformamide was treated with trans-dichlorobis(triphenylphosphine) palladium(II) (244 mg) and copper(II) iodide 66 mg) followed by triethylamine (7.52 mL), stirred under a nitrogen atmosphere for 5 min., treated with 3-hydroxyphenyl acetylene (2.467 g), stirred under nitrogen atmosphere for 16 h, poured into ethyl acetate and was washed with 0.05 N HCl and water. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, silica gel, 40% ethyl acetate/hexane as eluent, to afford 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol as a tan solid, 5.40 g; 1H NMR (DMSO-d6): delta 9.64 (s, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.27 (t, J=73.7 Hz, 1H), 7.17 (d, J=8.8 Hz, 2H), 7.16 (m, 1H), 6.94 (m, 1H), 6.86 (m, 1H), and 6.77 (m, 1H); MS (ES neg) m/z 260. EXAMPLE 81Preparation of 2-Amino-5-[4-(difluoromethoxy)phenyl]-5-(3hydroxyphenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one Step a) 3-((4-(Difluoromethoxy)phenyl)ethynyl)phenolA solution of 4-(difluoromethoxy)phenyl iodide (4.70 g) in deoxygenated dimethylformamide was treated with trans-dichlorobis(triphenylphosphine) palladium(II) (244 mg) and copper(II) iodide 66 mg) followed by triethylamine (7.52 mL), stirred under a nitrogen atmosphere for 5 min., treated with 3-hydroxyphenyl acetylene (2.467 g), stirred under nitrogen atmosphere for 16 h, poured into ethyl acetate and was washed with 0.05 N HCl and water. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, silica gel, 40% ethyl acetate/hexane as eluent, to afford 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol as a tan solid, 5.40 g; 1H NMR (DMSO-d6): delta 9.64 (s, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.27 (t, J=73.7 Hz, 1H), 7.17 (d, J=8.8 Hz, 2H), 7.16 (m, 1H), 6.94 (m, 1H), 6.86 (m, 1H), and 6.77 (m, 1H); MS (ES neg) m/z 260.

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, 1-(Difluoromethoxy)-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; US2009/48320; (2009); 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. 696-41-3, name is 3-Iodobenzaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C7H5IO

Triethyl phosphonoacetate (9.21 g, 41.12 mmol) in tetrahydrofuran (65 mL) was treated with 2.5 M n-butyl lithium in hexanes (12.82 mL, 32.07 mmol) at -78 C. The resulting mixture was stirred for 10 min and added via a cannula to a pre-cooled solution at -78 C of 3-iodobenzaldehyde (4.77 g, 20.56 mmol) in tetrahydrofuran (20 mL). The resulting mixture was stirred at -78 C for 40 min and slowly warmed to ambient temperature for 45 min. The reaction was quenched with saturated aqueous NH4Cl (200 mL). The aqueous solution was extracted with diethyl ether. The resulting organic layer was dried over magnesium sulfate and evaporated. The residue was purified by silica gel chromatography (90:10 hexanes/ethyl acetate) to give 5.71 g (92%) of compound 1a as a yellow oil; 1H NMR (CDCl3) delta 1.32 (t, J = 7.1 Hz, 3H); 4.24 (q, J = 7.1 Hz, 2H); 6.39 (d, J = 16.0 Hz, 1H); 7.09 (dd, J = J’ = 7.8 Hz, 1H); 7.43-7.46 (m, 1H); 7.54 (d, J = 16.0 Hz, 1H); 7.64-7.69 (m, 1H); 7.83-7.86 (m, 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:
Article; Fabio, Karine; Guillon, Christophe; Lacey, Carl J.; Lu, Shi-Fang; Heindel, Ned D.; Ferris, Craig F.; Placzek, Michael; Jones, Graham; Brownstein, Michael J.; Simon, Neal G.; Bioorganic and Medicinal Chemistry; vol. 20; 3; (2012); p. 1337 – 1345;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 627-31-6, 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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), This compound has unique chemical properties. The synthetic route is as follows.

Example 7; [0055] Synthesis of 3-(benzyloxy)-1 -(3-iodopropyl)pyridin-2(1 H)-one(Compound 7); To a solution of 1 ,3-diiodopropane (7.1 ml_, 63 mmol) in tetrahydrofuran (50 ml_) was added 3-(benzyloxy)pyhdin-2(1 H)-one (1.28 g, 6.3 mmol) and Na2CO3 (0.67 g, 6.3 mmol). The mixture was then stirred at 70 0C for 1 day. Reaction progress was monitored by ES-MS. After ESMS showed essentially complete consumption of the starting material 3-(benzyloxy)pyhdin-2(1 H)-one, the reaction was stopped. Then the reaction mixture was filtered, concentrated, and subjected to flash column chromatography (eluent: hexane : ethylacetate 1 :1 ). Compound 7 was obtained (240 mg, 10% yield). Analysis: ES-MS (positive ion in MeOH/H2O): m/z = 370.2, ([M+H]+, calculated: 370.03).

The chemical industry reduces the impact on the environment during synthesis 1,3-Diiodopropane(stabilized with Copper chip). I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOARD OF SUPERVISORS OF LOUISIANA STATE UNIVERSITY AND ARGRICULTURAL AND MECHANICAL COLLEGE; WO2008/100907; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com