Month: September 2021

Electric Literature of 63262-06-6, 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. 63262-06-6, name is 1,4-Dibromo-2,5-diiodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 2-(tributylstannyl)thiophene (20.7 g, 55.3 mmol) and1,4-dibromo-2,5-diiodobenzene (13.5 g, 27.7 mmol) in dry DMF (100 mL) was addedPd(PPh3)2Cl2 (0.78 g, 1.12 mmol). The mixture was stirred for 40 h at 80 C. Aftercooling to room temperature, the reaction mixture was poured into water and thenextracted with toluene. The combined organic layers were washed with water and driedover anhydrous Na2SO4. After filtration and evaporation, the crude product wasrecrystallized from methanol to provide 8 as a white solid (yield = 10.3 g, 93%).

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, 1,4-Dibromo-2,5-diiodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Komiyama, Hideaki; Adachi, Chihaya; Yasuda, Takuma; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1459 – 1466;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 41252-97-5, These common heterocyclic compound, 41252-97-5, name is 4-Iodo-2-nitrotoluene, 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 4-iodo-l-methyl-2-nitro-benzene (25.0 g, 107 mmol) in 300 mL of ethanol was added sulfided platinum (3.00 g) and ammonium formate (20.3 g, EPO 321 mmol). The mixture was heated to reflux for 12 h and then cooled to 22 C, filtered through Celite and concentrated in vacuo. The resulting residue was diluted with H2O (300 mL) and extracted with 3 x 200 mL CH2Cl2. The organic fractions were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to give b (21.1 g, 95%): MS m/z = 234 (M+H).

The synthetic route of 41252-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/41773; (2006); 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. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, A new synthetic method of this compound is introduced below., name: 1,2-Dichloro-4-iodobenzene

(R)-2-(3,4-Dichloro-phenylamino)-propionic acid (62% ee) A mixture of 6.00 g (22.00 mmol) 3,4-dichloroiodobenzene, 2.94 g (33.00 mmol) D-alanine, 0.42 g (2.20 mmol) copper(I) iodide, 0.96 g (4.40 mmol) 2-hydroxybenzaldehyde phenylhydrazone, 14.00 g (66.00 mmol) tri-potassium phosphate in 32 ml of N,N- dimethylformamide was stirred at 80C for 16 h under argon, then after cooling diluted with water and acidified to pH 3 by addition of 25% aq. HC1 solution. The mixture was extracted with EtOAc (3x), the organic phases were washed with brine, dried (Na2S04), filtered and evaporated. Flash chromatography (Si02; dichloromethane/MeOH 95:5 to 4:1) afforded 3.11 g (60%)) of the title compound (as 81 :19 mixture of the (R) and (S) stereoisomers, BGB- 175*0.25 column) as light brown solid. MS: 231.9 (M-FT, 2C1).

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; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; BINGGELI, Alfred; GREEN, Luke; HARTMANN, Guido; MAERKI, Hans P.; MATTEI, Patrizio; WO2011/48032; (2011); 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. 76801-93-9, name is 5-Amino-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide, A new synthetic method of this compound is introduced below., Computed Properties of C14H18I3N3O6

In a three-necked flask equipped with a stirrer and a reflux condenser,5-amino-N, N’-bis- (2,3-dihydroxypropyl) -2,4,6-triiodo-1,3-benzenedicarboxamide (84.6 g, 0.12 mol)N, N-dimethylacetamide (172 ml)Stir,Heated to 50 C dissolved, cooled to 10 C,A solution of chloroacetyl chloride (62 ml, 88.09 g, 0.78 mol)About 30min drop finished,The temperature was raised to 50 C for 3 h,Cooling to 0 ~ 10 ,At 10 ,Dropping 10 ml / L of sodium hydroxide solution 156 ml,Stir at room temperature for 1 h.After adding 100 ml of water, 59 ml of 1N hydrochloric acid was added dropwise, and the mixture was allowed to stand overnight. The filtrate was washed with water and dried to give 83.2 g of a yield of 90.0%.

The synthetic route of 76801-93-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiang Su Heng Rui Medicine Co., Ltd.; Hou, Xianshan; Wang, Junyan; Wang, Zhian; Zhong, Xinguang; (9 pag.)CN106278929; (2017); A;,
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

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. 20691-72-9, name is 4-Iodo-2-nitroaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5IN2O2

Commercial 4-iodo-2-nitroaniline was reduced with 5 eq tin dichloride dihydrate in ethanol solution (75 C., 2 h) to give 92% 4-iodo-1,2-phenylenediamine as light red solid.

The synthetic route of 20691-72-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, 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 755027-18-0, HPLC of Formula: C7H6BrIO

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 90C for 40 minutes, cooled to RT and poured into 2.4-L 1 M HCl. After stirring for 30 minutes, the solid was filtered, suspended in EtOH (230 mL) heated to reflux and allowed to cool to RT with stirring overnight. The solid was filtered and washed with 1 : 1 EtOH hexane (50 mL) to give the title compound. LRMS ESI+ (M+H)+ 257.0.

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; MERCK & CO., INC.; WO2008/57208; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6414-69-3, Adding some certain compound to certain chemical reactions, such as: 6414-69-3, name is Ethyl 3-iodopropanoate, 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 6414-69-3.

EXAMPLE VI Ethyl 2-Carboethoxy-3-indolepropanoate Ethyl 2-indolecarboxylate (3 gm), ethyl 3-iodopropanoate (5.4 gm), potassium carbonate (5 gm), and acetonitrile (50 ml) were combined and the mixture heated to reflux for 48 hours. The mixture was cooled and poured into water (50 ml). The mixture was extracted with ether (3*75 ml) and the combined ether extracts were washed with water (3*30 ml). The organic layer was dried over sodium sulfate and the solvent removed on a rotary evaporator. The diester product was obtained as a colorless oil.

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 6414-69-3.

Reference:
Patent; C.D. Searle & Co.; US5137910; (1992); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 25252-00-0, 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 25252-00-0 as follows.

Part C. 3′-(1-benzyl-6-cyano-1H-indol-3-ylmethyl)-4-carbamoyl-biphenyl-2-carboxylic acid benzyl ester:; 2-Bromo-5-iodobenzoic acid (6.54 g, 20.0 mmol) was dissolved in DMF (70 mL). Potassium bicarbonate (2.2 g, 22.0 mmol) was added, followed by benzyl bromide (2.8 mL, 22.0 mmol). The mixture was stirred at rt under N2 for 12 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organic solution was washed with brine, dried over MgSO4, and concentrated and dried to give 9.05 g of the benzyl ester. The ester (2.3 g, 7.69 mmol), Zn(CN)2 (1.3 g, 11.5 mmol), and Pd[PPh3]4 were dissolved together in 25 mL of DMF. The mixture was de-gassed and heated at 90 C. for 4 h. Reaction mixture was concentrated and purified by chromatography (silica gel, 5% EtOAc in hexane) to give 1.8 g of the benzonitrile. MS: 316.0, 317.9 (M+1)+. The benzonitrile (1.4 g, 4.4 mmol) was dissolved in 15 mL of DMF. The reaction mixture was cooled at 0 C. Potassium carbonate (0.20 g, 1.45 mmol) was added, followed by dropwise addition of 30% hydrogen peroxide solution (1.2 mL). The cooling bath was removed and the mixture was stirred at rt for 12 h. The reaction was quenched with aqueous NaHSO3 and water. The formed precipitate was filtered and dried to give 1.1 g of the desired amide. MS: 334.2, 336.3 (M+1)+. A mixture of the resulting amide (0.2 g, 0.6 mmole), bis(pinacolato)diboron (0.228 g, 0.9 mmol) and anhydrous KOAc (0.18 g, 1.8 mmol) in 2 mL of 1,4-dioxane was purged with argon, then (1,1′)-bis(diphenylphosphino)ferrocene)palladium(II) chloride (20 mg, 0.024 mmol) was added. The resulting mixture was heated in a sealed tube in a microwave reactor at 100 C. for 2 h then left standing overnight at rt. The reaction was diluted with water and extracted 3× with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the boronate (0.13 g, 57%). A mixture of this compound, the compound of Part B (0.1 g, 0.25 mmol), and K3PO4 (0.11 g, 0.5 mmol) in 5 mL dioxane was degassed and then treated with tetrakis(triphenylphosphine)palladium(20 mg, 0.017 mmol). The resulting mixture was heated in a 95-100 C. oil bath under N2 for 2 h, then stirred at rt overnight. The reaction mixture was diluted with brine and extracted 3× with EtOAc. The combined extracts were washed with brine then dried over anhydrous Na2CO3, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the product (0.12 g, 83%) as a light yellow foam. 1H NMR (400 MHz, CDCl3) delta ppm 4.07 (s, 2H) 4.90 (s, 2H) 5.23 (s, 2H) 6.91 (d, J=6.15 Hz, 2H) 7.05 (m, 3H) 7.20 (m, 6H) 7.29 (m, 5H) 7.42 (d, J=7.91 Hz, 1H) 7.51 (d, J=10.99 Hz, 2H) 7.98 (dd, J=8.13, 1.98 Hz, 1H) 8.19 (d, J=2.20 Hz, 1H). LC/MS m/z 576.16 (M+H)+.

According to the analysis of related databases, 25252-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 887266-99-1,Some common heterocyclic compound, 887266-99-1, name is 3-Fluoro-4-iodobenzonitrile, molecular formula is C7H3FIN, 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 1: (4-Cyano-2-fluorophenyl)boronic acid 24.3 ml (48.6 mmol) of a 2 M solution of isopropylmagnesium chloride in diethyl ether were added dropwise to a solution of 10.0 g (40.5 mmol) of 3-fluoro-4-iodobenzonitrile in a mixture of 120 ml of anhydrous THF and 120 ml of anhydrous diethyl ether at -78 C. When the addition had ended, the mixture was stirred further at -78 C. for another 75 min. 15 ml (64.8 mmol) of triisopropyl borate were then added dropwise. The mixture was then stirred at -78 C. for a further 15 min, before the cold bath was removed and the reaction mixture was allowed to warm to RT. After 3 h at RT, 80 ml of 2 M hydrochloric acid were added and the mixture was stirred intensively at RT for 20 min. Thereafter, it was diluted with approx. 400 ml of water. The phases were separated and the aqueous phase was extracted three times with approx. 150 ml of ethyl acetate each time. The combined organic extracts were washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the mixture was filtered and the filtrated was concentrated to dryness on a rotary evaporator. 3.68 g (55% of th.) of the title compound were obtained, this being employed for subsequent reactions without further purification. LC/MS (method F, ESIneg): Rt=0.53 min, m/z=164 [M-H]-.

The synthetic route of 887266-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; Haerter, Michael; Beck, Hartmut; Ellinghaus, Peter; Berhoerster, Kerstin; Greschat, Susanne; Thierauch, Karl-Heinz; Suessmeier, Frank; US2013/196964; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com