Month: June 2021

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. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,2-Dichloro-4-iodobenzene

[0268] To a solution of 1,2-dichloro-4-iodobenzene (1.0 g, 3.68 mmol) in ether (10 mL) at 0 C. was added iPrMgCl (2.2 mL, 2M in Et2O) dropwise and the resulting solution stirred at 0 C. for 30 minutes and room temperature 1 hour. The reaction mixture was recooled to 0 C. and cyclopropylacetonitrile (0.34 mL, 1.0 eq.) was added. The reaction mixture was stirred at 0 C., room temperature 1 hour, then quenched by the addition of 1N HCl. The resulting solution was stirred at room temperature 2 hours and extracted with CH2Cl2. The combined organics were dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography using a 100% hexanes to 10% EtOAc in hexanes solution gradient as eluent (0.10 g, 21% yield). LCMS: MH+=227.

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 20555-91-3.

Reference:
Patent; Schering Corporation; US2003/232837; (2003); 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. 6293-83-0, name is 2-Iodo-4-nitroaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 6293-83-0

To the solution of 2-iodo-4-nitroaniline (3.0 g, 11 mmol) in DMF (60 mL) and Et3N (60 mL) was added 2-ethynylpyridine (3.0 g, 45 mmol), Pd(PPh3)2Cl2 (600 mg) and CuI (200 mg) under N2. The reaction mixture was stirred at 60 C. for 12 h. The mixture was diluted with water and extracted with dichloromethane (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by chromatography on silica gel (5-10% ethyl acetate/petroleum ether) to afford 4-nitro-2-(pyridin-2-ylethynyl)aniline (1.5 g, 60%). 1H NMR (300 MHz, CDCl3) delta 8.60 (s, 1H), 8.13 (d, J=2.1 Hz, 1H), 7.98 (d, J=1.8, 6.9 Hz, 1H), 7.87-7.80 (m, 2H), 7.42-7.39 (m, 1H), 7.05 (brs, 2H), 6.80 (d, J=6.9 Hz, 1H).

According to the analysis of related databases, 6293-83-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hadida Ruah, Sara S.; Grootenhuis, Peter D.J.; Van Goor, Frederick; Zhou, Jinglan; Bear, Brian; Miller, Mark T.; McCartney, Jason; Numa, Mehdi Michel Jamel; US2007/244159; (2007); 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. 20691-72-9, name is 4-Iodo-2-nitroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Iodo-2-nitroaniline

4-iodo-2-nitroaniline (2.64 g, 10.0 mmol)Was dissolved in 80% ethanol (60 mL)Concentrated hydrochloric acid (2.5 mL) was added.Iron powder (2.23 g, 40.0 mmol) was added,And the mixture was heated under reflux for 6 hours under stirring.After returning to room temperature,The precipitate was filtered,The solvent was distilled off under reduced pressure.After extraction with ethyl acetate (100 mL × 2) and saturated aqueous sodium hydrogen carbonate solution,The organic layer was washed with saturated brine.After dehydration with anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure,The residue was subjected to silica gel column chromatography using ethyl acetate / hexane (1/1 (volume ratio)) as an elution solvent,Compound 9 was obtained in a yield of 1.98 g (89.1%).

According to the analysis of related databases, 20691-72-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyoto University; Nihon Medi-Physics Co.,Ltd.; Saji, Hideo; Ono, Masahiro; Inohara, Tadashi; Seki, Ikuya; (24 pag.)JP2016/79108; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Phosphorus oxychloride (1.47 g, 9.6 mmol, 0.9 mL) was added dropwise at -10 C to a stirred pyridine (40 mL) solution of N-Boc-L-proline 7 (1.74 g, 8.08 mmol) and arylamine 6 (2.24 g, 8.08 mmol) under argon atmosphere. The reaction mixture was stirred for 30 min (-10-5 C), then poured into water (200 mL) containing ice, and extracted with EtOAc. The aqueous layer was additionally extracted with EtOAc. The extract was washed with water, saturated NaHCO3 solution, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel using CHCl3 as the eluent. The isolated product with Rf 0.56 (EtOAc/LP, 1 : 2) was crystallized from petroleum ether to give amide 8 (2.8 g, 74%) as light brown crystals, m.p. 92-95 C, [alpha]23D -103.96 (c = 1.0, CHCl3). 1H NMR (CDCl3), delta: 1.35 and 1.49 (both br.s, integral ratio of 5/4, 9 H, Me3C); 1.74-2.42 (m, 4 H, HC(4), HC(5)); 3.39-3.80 (m, 2 H, HC(3)); 3.91 (s, 3 H, MeO); 4.27 and 4.41 (both m, integral ratio of 5/4, 1 H, HC(1)); 7.81 (br.d, 1 H, HC(3), J = 8.2 Hz); 8.34 (br.s, 1 H, HC(4)); 8.57 (br.d, 1 H, HC(6), J = 8.2 Hz); 11.43 (m, 1 H, HN) (mixture of rotamers, see Ref. 21).

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, Methyl 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lozanova; Stepanov; Mel?nik; Zlokazov; Veselovsky; Russian Chemical Bulletin; vol. 68; 1; (2019); p. 64 – 67; Izv. Akad. Nauk, Ser. Khim.; 1; (2019); p. 64 – 67,4;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 6940-76-7, 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. 6940-76-7 name is 1-Chloro-3-iodopropane, 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.

To a solution of TMEDA (4.36 mL, 28.9 mmol) in THF (30 mL) at -20 C was added n- butyllithium (12.03 mL, 28.9 mmol, 2.4 M solution in hexanes) over ten minutes. The mixture was stirred at 10 C for 30 minutes, then cooled to -78 C, and a solution of tert- butyl (6-chloropyridin-2-yl)carbamate (3 g, 13.12 mmol) in THF (15 mL) was added over a period of 5 minutes. After 40 minutes, copper(I) iodide (2.499 g, 13.12 mmol) was added, and the mixture was stirred at -10 C for 1 hour. l-Chloro-3-iodopropane (2.113 mL, 19.68 mmol) was added over a period of 1 minute, and the mixture was allowed to reach room temperature. After 2.5 hours the mixture was added to saturated aqueous sodium hydrogencarbonate and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was stirred in dichlorom ethane (30 mL), filtered through a glass- sintered funnel and concentrated to half volume and then applied onto a flash column (120 g silica), eluting with 2-20% ethyl acetate in heptane. The eluent coming off the column was passed through a column of potassium carbonate. This gave the desired product tert-butyl 7- chloro-3,4-dihydro-l,8-naphthyridine-l(2H)-carboxylate (2.637 g). Yield 74% NMR (400 MHz, Chlorofomwf) d 7.32 (d, J = 7.9 Hz, 1H), 6.94 (d, J = 7.8 Hz, 1H), 3.81 – 3.69 (m, 2H), 2.73 (t, J= 6.6 Hz, 2H), 1.93 (p, J= 6.5 Hz, 2H), 1.54 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Chloro-3-iodopropane, and friends who are interested can also refer to it.

Reference:
Patent; MORPHIC THERAPEUTIC, INC.; HARRISON, Bryce, A.; DOWLING, James, E.; GERASYUTO, Aleksey, I.; BURSAVICH, Matthew, G.; TROAST, Dawn, M.; LIPPA, Blaise, S.; ROGERS, Bruce, N.; ZHONG, Cheng; QIAO, Qi; LIN, Fu-Yang; SOSA, Brian; BORTOLATO, Andrea; SVENSSON, Mats, A.; HICKEY, Eugene; KONZE, Kyle, D.; DAY, Tyler; KIM, Byungchan; (124 pag.)WO2020/47208; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 618-91-7,Some common heterocyclic compound, 618-91-7, name is Methyl 3-iodobenzoate, molecular formula is C8H7IO2, 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 methyl 3-iodobenzoate (4.5 g, 17.2 mmol) in DMSO (30 mL) was added 3-azetidin-3-ol hydrogen chloride salt (1.3 g, 11.8 mmol), Cs2CO3 (9.5 g, 29.2 mmol), CuI (446 mg, 2.3 mmol) and L-proline (540 mg, 4.7 mmol) and then the mixture was heated at 90 C. for 18 h under argon atmosphere. The solution was diluted with EA and water and the organic layer was washed with brine three times, concentrated under reduced pressure and purified by CC (PE/EA=2:1) to give compound 3a (1.6 g, 66%) as a yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-iodobenzoate, its application will become more common.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; Kinzel, Olaf; Steeneck, Christoph; Kremoser, Claus; US2014/221659; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 111771-08-5, name is 2-Fluoro-6-iodobenzoic acid, molecular formula is C7H4FIO2, 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: C7H4FIO2

(2-Fluoro-6-iodophenyl)methanol.; To a stirred solution of 2-fluoro-6-iodobenzoic acid (10 mmol) in THF (6.5 mL) and trimethylborate (3.25 mL) was added borane dimethylsulfide (12 mmol) slowly, maintaining the internal temperature at 20-25 C. Stirring was continued for an additional 16 h at room temperature and then methanol (1.44 mL) was added cautiously. The resulted solution was evaporated in vacuo to offer 2.5 g of the title compound as a pale yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 111771-08-5, its application will become more common.

Reference:
Patent; PHARMACOPEIA, INC.; US2008/85898; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 202865-85-8, name is 1-Bromo-4-iodo-2-methylbenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 202865-85-8

Carbazole (1.67 g, 10 mmol), 2-bromo-5-iodobenzene (1.57 ml, 2.07 g/mL, 11 mmol), cuprous iodide(0.38 g, 0.2 mmol) and sodium tert-butoxide (1.92 g, 20 mmol) were added to the reaction flask, and nitrogen gas was exchanged three times (10 min/time), and the solvent (1,4-dioxane) was injected under a nitrogen atmosphere. After the raw material is partially dissolved, 2 ml of 1,2-diaminocyclohexane is injected (withAfter the injection, the reaction was refluxed at 110 C for 6 h, extracted, concentrated, and powdered, and purified by column chromatography to obtain a white solid product 2 in a yield of 70%.

The synthetic route of 202865-85-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; South China University of Technology; Tang Benzhong; Zhao Zujin; Hu Shimin; Qin Anjun; Hu Rongrong; Wang Zhiming; (24 pag.)CN109593079; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 61272-76-2, 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. 61272-76-2 name is 4-Fluoro-2-iodoaniline, 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.

N-(4-Fluoro-2-iodophenyl)acetamide (Ian-08) A solution of acetyl chloride (2.55 g, 25.2 mmol) in anhydrous dichloromethane (10 ml) was added at 0° C. to a solution of 4-fluoro-2-iodoaniline (Ian-04) (5.93 g, 25 mmol) and triethylamine (3.5 ml) in anhydrous dichloromethane (10 ml). The mixture was stirred for 1 h at 0° C. and then overnight at room temperature and then made alkaline with 25percent potassium carbonate solution. The phases were separated and the aqueous phase was extracted with dichloromethane (2*30 ml). The combined organic phases were dried with sodium sulfate and concentrated to small volume under vacuum. The residue (7.01 g) was taken up in tetrahydrofuran (120 ml) and filtered. The filtrate was concentrated to small volume under vacuum. Yield: 6.60 g (95percent), white solid Melting point: 142-144° C. 1H-NMR (DMSO-d6): 2.03 (s, 3H); 7.25 (dt, 1H, J=8.6, 2.9 Hz); 7.37 (dd, 1H, J=8.8, 5.7 Hz); 7.75 (dd, 1H, J=8.2, 2.9 Hz); 9.46 (s, 1H).

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

Reference:
Patent; GRUNENTHAL GMBH; US2009/215725; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 4387-36-4, name is 2-Iodobenzonitrile, 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 4387-36-4, COA of Formula: C7H4IN

Preparation 1; 4′-Bromo-biphenyl-2-carbonitrile Combine 2-iodobenzonitrile (9. 0g, 38.5 mmol), 4-bromophenylboronic acid (10.4g, 51.8 mmol), 2M aqueous sodium carbonate (20 mL) and tetrakis (triphenylphosphine)- palladium (O) (4. 5g, 3.9 mmol) in 300 mL of dioxane and heat to 80°C under nitrogen with stirring. After 3 hours cool to room temperature and dilute with 900 mL of ethyl acetate. Wash with water (2 x 50mL), brine (1 x 50mL) and dry over sodium sulfate. Filter and evaporate to a yellow solid. Chromatograph on silica gel two times, eluting with a gradient of 100percent toluene to 1/9 ethyl acetate/toluene to give the title compound as a tan solid, 5.42 g (55percent). MS (FAB) = 257 (M) ; HPLC analysis is 95percent.

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/70916; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com