Month: April 2021

Application of 335349-57-0,Some common heterocyclic compound, 335349-57-0, name is 5-Chloro-4-iodo-2-nitroaniline, molecular formula is C6H4ClIN2O2, 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 suspension of 5-chloro-4-iodo-2-nitroaniline (Intermediate 6, 36.5 g, 122 mmol) in EtOH (800 niL) and water (150 mL) was added iron powder (38 g, 673mmol) and NH4Cl (16 g, 306 mmol). The mixture was heated under nitrogen at 5O0C overnight. Additional iron powder (38 g, 673 mmol) and NH4Cl (16 g, 306 mmol) were added and heating was continued for 45 h. The reaction mixture was cooled, filtered and concentrated. The residue was re-dissolved in ethyl acetate and washed with sodium bicarbonate solution. The organic phase was concentrated to afford the desired product as a gray solid, which was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-4-iodo-2-nitroaniline, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; METABASIS THERAPEUTICS, INC.; DANG, Qun; CHUNG, De Michael; GIBSON, Tony, S.; JIANG, Hongjian; CASHION, Daniel, K.; BAO, Jianming; LAN, Ping; LU, Huagang; MAKARA, Gergely, M.; ROMERO, F. Anthony; SEBHAT, Iyassu; WODKA, Dariusz; WO2010/51206; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 16932-44-8, These common heterocyclic compound, 16932-44-8, name is 2-Iodo-1,3-dimethoxybenzene, 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 5 mL microwave reaction tube (Biotage Inc.) equipped with a stir bar was added 21c or 21e (1 mmol), 10% Pd/C (0.04 mmol), triphenylphosphine (0.16 mmol), copper (I) iodide (0.16 mmol), trimethylsilylacetylene (1.05 mmol), triethylamine (3 mL) and acetonitrile (2 mL). The microwave tube was sealed with a crimp-cap and subjected to microwave heating in a microwave reactor (Initiator, Biotage Inc.) set at 120 C with ?fixed hold time? for 5 min. At the end of the reaction, the grey-black suspension was passed through Celite pad, washing thoroughly with hot ethyl acetate (20 mL). The filtrate concentrated in reduced pressure and silica gel (1 g) was added. Further evaporation lead to a silica gel plug which was loaded on top of a silica gel column (2 cm ¡Á 20 cm) and eluted with 5% ethyl acetate in hexanes. Fractions corresponding to the product spot were evaporated under reduced pressure to obtain an analytically pure product.

The synthetic route of 16932-44-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gangjee, Aleem; Namjoshi, Ojas A.; Keller, Staci N.; Smith, Charles D.; Bioorganic and Medicinal Chemistry; vol. 19; 14; (2011); p. 4355 – 4365;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 6293-83-0, 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. 6293-83-0 name is 2-Iodo-4-nitroaniline, 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.

General procedure: In a typical reaction, PdCl2(PPh3)2 (88 mg, 0.125 mmol), CuI (24 mg, 0.125 mmol) and THF (5 ml) were placed in an oven-dried, 2-neck RB flask. To this suspension, 2-iodoaniline (5.47 mg, 2.5 mmol) and triethylamine (702 mul, 5.0 mmol) were added. The reaction mixture was degassed by bubbling with argon for 15 min. Phenylacetylene (300 mul, 2.75 mmol) was then added, and the reaction mixture stirred at RT. After complete consumption of the 2-iodoanilines (~2 h, by TLC), the reaction mixture was filtered through celite, and the solvent rotary evaporated to obtain the crude product which was purified by silica gel (60-120 mesh) column chromatography using ethylacetate/ hexane (1:9, v/v) as eluent to give pure 2-phenylethynylaniline, 2a (400 mg, 83%).

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

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 55; 40; (2014); p. 5495 – 5498;,
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. 31827-94-8, name is 2-Bromo-1-(4-iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-1-(4-iodophenyl)ethanone

General procedure: The appropriate carbonyl compound (50 mmol) was dissolved in 50 mL of ethanol and magnetically stirred with an equimolar quantity of thiosemicarbazide for 24 h at room temperature with catalytic amounts of acetic acid. The desired thiosemicarbazone precipitated from reaction mixture, was filtered, crystallized from suitable solvent, and dried. Equimolar quantities of 4-iodo-acetophenone and bromine, both dissolved in chloroform, were stirred for 4 h at room temperature until the presence of HBr disappeared. The solution was evaporated under vacuum and the obtained pale yellow solid was washed with petroleum ether to give alpha-bromo-4-iodo-acetophenone in good yield (94%). Equimolar amounts of the prepared thiosemicarbazone (50 mmol) and alpha-bromo-4-iodo-acetophenone (50 mmol), both suspended in 50 mL of ethanol, were reacted at room temperature under magnetic stirring for 10 h. The precipitate was filtered and purified by chromatography to give compounds 1-25 in high yield.

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 31827-94-8.

Reference:
Article; Secci, Daniela; Bizzarri, Bruna; Bolasco, Adriana; Carradori, Simone; D’Ascenzio, Melissa; Rivanera, Daniela; Mari, Emanuela; Polletta, Lucia; Zicari, Alessandra; European Journal of Medicinal Chemistry; vol. 53; (2012); p. 246 – 253;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 181765-86-6, These common heterocyclic compound, 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, 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.

In a 500-mL round-bottom flask reactor, methyl 5-bromo-2-iodobenzoate (25.0 g, 73 mmol), 4-dibenzofuran boronic acid (18.7 g, 88 mmol), tetrakis (triphenylphosphine)palladium (1.7 g, 0.15 mmol), and potassium carbonate (20.2 g, 146.7 mmol) were stirred together with toluene (125 mL), tetrahydrofuran (125 mL), and water (50 mL) for 10 hrs at 80 C. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer thus formed was separated, concentrated in a vacuum, and purified by column chromatography to afford (75.0 g, 60.1%).

Statistics shows that Methyl 5-bromo-2-iodobenzoate is playing an increasingly important role. we look forward to future research findings about 181765-86-6.

Reference:
Patent; SFC CO., LTD.; LEE, Chang-Hee; SEO, Hyun-JONG; YOON, Seo-Yeon; SHIM, So Young; KIM, Si-In; (214 pag.)US2018/233669; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 51839-15-7, These common heterocyclic compound, 51839-15-7, name is Dimethyl 5-iodoisophthalate, 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.

Dimethyl-5-iodoisophthalate (1.35 g, 4.21 mmol, Matrix Scientific, Columbia, SC) and lithium hydroxide monohydrate (884 mg, 20.07 mmol) were taken in a mixture of 3.95 mL methanol and 0.99 mL water and the suspension was stirred vigorously at 20 C for 3.5 h. The mixture was diluted with aqueous saturated sodium bicarbonate to a volume of 75 mL, and unreacted ester was removed by extraction with 75 mL ethyl acetate. The aqueous layer was carefully acidified with 1 M HCl to pH 2 and the resultant acid was extracted twice with 250 mL ethyl acetate. The ethyl acetate fractions were combined, dried over sodium sulfate, and the ethyl acetate was evaporated to give a white powder (965 mg, 78.4%): mp 302-303 C 1H NMR-300 MHz (CD3OD) delta 8.55 (d, 2H), 8.60 (d, 1H). 13C NMR (126 MHz, CD3OD) delta 92.6, 129.5, 132.6, 142.2, 165.7. MS (LCMS-ESI; negative ion mode) m/z: 290.7 (M-H)-; HRMS (FAB-) Calcd for C8H4IO4 (M-H)- 290.9154. Found 290.9141 ¡À 0.0000 (n = 2).

The synthetic route of 51839-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vaidyanathan; White; Affleck; Zhao; Welsh; McDougald; Choi; Zalutsky; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 6929 – 6939;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 31599-61-8,Some common heterocyclic compound, 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, molecular formula is C8H9I, 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 mixture of aryl halide (2.0 mmol), phenyl boronic acid (0.244 g, 2.0 mmol), the palladium complex 5a (0.001 mmol) and potassium carbonate (0.232 g, 4.0 mmol) in THF (15 ml)/DMF (15 mL) was refluxed for 1.5 h, as mentioned in Table 3. After 1.5 h, the solvent was evaporated and the reaction mixture wasextracted with diethyl ether. The ether solution was dried over Na2SO4, filtered and passed through a 1200 silica column (60-120 mesh). After evaporation of the ether, solid pure products were obtained. The yields of the products obtained from all the reactions were determined after isolation and the products were characterizedby their 1H NMR spectra (Table 6).

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-1,2-dimethylbenzene, its application will become more common.

Reference:
Article; Pattanayak, Poulami; Pratihar, Jahar Lal; Patra, Debprasad; Brandao, Paula; Felix, Vitor; Chattopadhyay, Surajit; Polyhedron; vol. 79; (2014); p. 43 – 51;,
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. 13421-13-1, name is 4-Chloro-2-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Chloro-2-iodobenzoic acid

Sodium hydroxide (15.3g, 272mmol) in 180mL water solution of the 4- chloro-2-benzoic Acid iodide (15.4g, 54.5mmol), copper powder (0.346g, 5.5mmol), thiophenol (5.57mL, 54.5 It was placed mmol). After heating the reaction mixture solution to 120 C to proceed the reaction for 8 hours, it was passed through Celite and the filtered to remove the copper. While the mixed solution was filtered and stirred to progress after cooling to room temperature, it was added an excess of aqueous HCl solution (5M, 100mL). The resulting white solid was filtered and dried under reduced pressure after washing with excess water under reduced pressure to give the title compound as a white solid (13.7g, 95%).

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 13421-13-1.

Reference:
Patent; Dongwoo Fine-Chem.,Ltd.; Jo, Sung Hyun; Kim, Hyun Woo; (11 pag.)KR2015/15102; (2015); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 624-75-9, name is 2-Iodoacetonitrile, 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 624-75-9, Quality Control of 2-Iodoacetonitrile

Example 112b Methyl 3-(Cyanomethyl)-5,6,7,8-tetrahydroindolizine-2-carboxylate 112b A 500-mL three-neck round-bottomed flask equipped with an addition funnel, thermometer and charged with 112a (6.70 g, 37.4 mmol), Iodoacetonitrile (12.5 g, 74.9 mmol), iron (II) sulfate heptahydrate (5.20 g, 18.7 mmol) and dimethyl sulfoxide (250 mL). Hydrogen peroxide (35%, 18.2 g, 187 mmol) was added dropwise to the mixture in 1 h through a syringe pump at room temperature using a water bath. Iron (II) sulfate heptahydrate (2 to 3 equivalent) was added to the reaction mixture in portions to keep the temperature between 25 C to 35 C, until the color of the reaction mixture is deep red. If TLC shows the reaction not completed, then more hydrogen peroxide (2-3 equivalent) and more iron (II) sulfate heptahydrate (1-2 equivalent) are added in the same manner until the reaction is completed. After that time, the reaction mixture was partitioned between saturated sodium bicarbonate solution (200 mL) and ethyl acetate (400 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2 * 100 mL). The combined organic layers were washed with saturated Sodium thiosulfate solution (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 78% yield (6.40 g) of 112b as a yellow oil: 1H NMR (500 MHz, CDCl3) delta 6.23 (s, 1H), 4.23 (s, 2H), 3.94 (t, 2H, J = 6.5 Hz), 3.81 (s, 3H), 2.74 (t, 2H, J = 6.5 Hz), 2.00 (m, 2H), 1.83 (m, 2H); (APCI+) m/z 219.3 (M+H)

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

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 14452-30-3, A common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, molecular formula is C8H7IO, 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.

Example 63; 5-[1-(3-Iodophenyl)-ethoxy]-quinazoline-2,4-diamine; [00203] Step 1; To a cold (ice water) solution of 3-iodoacetophenone (2.59 gm; 10.5 mmol) in methanol (10 mL) is added sodium borohydride (395 mg; 10.4 mmol) is stirred for thirty minutes. Water (10 mL) is added to the solution and stirred 15 minutes. Saturated ammonium chloride (40 mL) is added and the solution is extracted with ethyl acetate. The organics are separated and dried over magnesium sulfate. The solvent is removed to give 2.26 grams of 1-(3-iodophenyl)-ethanol.

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; DECODE CHEMISTRY, INC.; SINGH, Jasbir; GURNEY, Mark E.; WO2005/123724; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com