Category: iodides-buliding-blocks

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 23399-70-4 as follows. COA of Formula: C7H6ClI

Step 2: At O0C5 a solution of 4-chloro-l-iodo-2-methylbenzene (642 mg, 2.53 mmol) in 5mL of pentane was treated with t-BuLi (1.68 mL of 1.7 M in pentane solution, 2.86 mmol) slowly, and stirred for 30 min. The resulting yellow mixture was cooled to – 60 0C, and a solution of N-methoxy-N-methyl-l-(trifluoroinethyl)cyclopropanecarboxamide (346 mg, 1.75 mmol) in 3.0 mL of THF was added via syringe. The reaction mixture was slowly warmed to RT in 1 h, then partitioned between a mixture of sat. ammonium chloride and EtOAc. The organic layer was separated, dried and concentrated. Purification of the residue on the ISCO (12 g column, 0-10% EtOAc:Hexanes) provided the title compound (384 mg, 83%) as a colorless amorphous solid. MS (ESI3 pos. ion) m/z: 263.1 (M+l).

According to the analysis of related databases, 23399-70-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; TASKER, Andrew; ZHANG, Dawei; WO2008/30466; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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. Computed Properties of C2H2IN

The compound obtained in Example 64 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and the residue was treated in water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of regioisomers as yellow oil. These two regioisomers (4.16 g, 80%) were used in the next reaction step without separation.Example 65-2Preparation of 4-(2-chloropyridin-5-yl)-5-(3-methoxy-5-methylphenyl)-pyrazol-1-yl)acetonitrile1H NMR (CDCl3) delta 2.28 (s, 3H), 3.66 (s, 3H), 5.16 (s, 2H), 6.71 (s, 2H), 6.84 (s, 1H), 7.24 (d, J=8.3 Hz, 1H), 7.49 (dd, J=2.3, 5.9 Hz, 1H), 7.70 (s, 1H, 8.32 (s, 1H); 13C NMR (CDCl3) delta 21.57, 39.89, 55.23, 110.80, 113.76, 115.28, 117.76, 121.47, 124.02, 127.24, 129.92, 132.57, 138.58, 140.12, 148.71, 149.92, 151.17, 159.69, 162.33.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 65 (0.3 g, 0.89 mmol), 3-pyridineboronic acid (0.13 g, 1.07 mmol), dichlorobis(triphenylphosphine)palladium (II) (32 mg, 0.05 mmol) and potassium carbonate (0.13 g, 0.89 mmol). The reaction system was purged with nitrogen gas for 10 min, and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:3, v/v): (87 mg); m.p. 64-65 C.; in NMR (CDCl3) delta 2.37 (s, 3H), 3.79 (s, 3H), 4.94 (s, 2H), 6.71 (s, 1H), 6.77 (s, 1H), 6.88 (s, 1H), 7.36-7.40 (m, 1H), 7.60-7.67 (m, 2H), 7.92 (s, 1H), 8.27 (d, J=7.7 Hz, 1H), 8.60-8.62 (m, 2H), 9.15 (s, 1H); 13C NMR (CDCl3) delta 21.60, 37.81, 55.41, 112.42, 114.14, 116.71, 118.30, 120.26, 122.69, 123.62, 127.25, 128.99, 134.09, 134.43, 135.01, 139.48, 141.21, 141.39, 147.98, 148.25, 149.80, 152.64, 160.40.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 624-75-9, its application will become more common.

Reference:
Patent; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 17024-12-3 as follows. HPLC of Formula: C14H9I

Mixed under argon flow were 100 g of 1-aminonaphthalene (manufactured by Aldrich Co., Ltd.), 255 g of 9-iodophenanthrene, 204 g of anhydrous potassium carbonate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 4.7 g of copper powder (manufactured by Hiroshima Wako Co., Ltd.) and 750 ml of decalin, and they were reacted at 190C for 3 days. After cooling, 2 liter of toluene was added thereto to filter an insoluble matter. The matter filtered was dissolved in 4.5 liter of chloroform to filter off an insoluble matter, and then the filtrate was treated with activated carbon and concentrated under reduced pressure. Acetone 3 litter was added when the solution became slurry in the middle of concentration, and crystal deposited was filtered and refined through a column. Mixed under argon flow were the powder obtained, 200 g of 4-bromoiodobenzene (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 204 g of anhydrous potassium carbonate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 4.7 g of copper powder (manufactured by Hiroshima Wako Co., Ltd.) and 750 ml of decalin, and they were reacted at 190C for 3 days. After cooling, 2 liter of toluene was added thereto to filter an insoluble matter. The matter filtered was dissolved in 4.5 liter of chloroform to filter off an insoluble matter, and then the filtrate was treated with activated carbon and concentrated under reduced pressure. Acetone 3 litter was added when the solution became slurry in the middle of concentration, and crystal deposited was filtered. This was refined through a column and dissolved in toluene, and hexane was added thereto to reprecipitate crystal. It was filtered and then dried to obtain 64 g of N-(4-bromophenyl)-N-(phenantho-9-yl)-1-naphthylamine (B8).

According to the analysis of related databases, 17024-12-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1559706; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 460-37-7, The chemical industry reduces the impact on the environment during synthesis 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, I believe this compound will play a more active role in future production and life.

5-Ch[oro-N-(piperidin-4-y[)pyrazine-2-carboxamide trifluoroacetic acid salt[Intermediate 68] (722 mg, 3.00 mmol, 1 .0 eq), and potassium carbonate (2.07 g, 15.0 mmol, 5.0 eq) were suspended in 33 mL acetonitrile. Then, 1,1,1- trifluoro-3-iodopropane [CAS RN: 460-37-7] (1.01 g, 4.50 mmol, 1.5 eq) was added and the reaction mixture was heated to 70C for 4 h. On cooling, the reaction mixture was diluted with water and extracted withdichloromethane/isopropanol (4/1) (2x). The combined organic phases were washed with brine. Phase separation was conducted by the use of a Whatman filter. The volatile components were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 50 g SNAP cartridge:dichloromethane -> dichloromethane/ethanol 95/5) to give 900 mg (41% yield oftheory) of the title compound.UPLC-MS (Method 1): R = 0.58 mm; MS (ESI0): m/z = 337 [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, 1,1,1-Trifluoro-3-iodopropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 124700-41-0, 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. 124700-41-0, name is 2-Fluoro-5-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Fluoro-5-iodobenzoic acid (6.60 g, 24.81 mmol) was dissolved in chloroform (70 ml) and oxalyl chloride (4.30 ml, 49.29 mmol) and dimethylformamide (catalytic amount) were added. The mixture was stirred at room temperature for 3 hrs. The reaction solution was concentrated under reduced pressure and chloroform (35 ml), was added to dissolve the residue. The obtained solution was added dropwise to a solution of ethyl 3,3-dimethylaminoacrylate (4.26 g, 29.75 mmol) and triethylamine (5.19 ml, 37.24 mmol) in chloroform (35 ml), and the mixture was stirred at room temperature for 15 hrs. Water was added to partition the reaction solution, and the organic layer was washed with saturated brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel chromatography (ethyl acetate_hexane=1:2 to 1:1) to give an object product (6.40 g, yield 66%) of a mixture of E form and Z form as an orange solid.1H NMR(CDCl3 400MHz) (delta) ppm: 0.94 (3H, t, J=7.2Hz), 2.88 (3H, brs), 3.31 (3H, brs), 3.97 (2H, q), 6.78 (1H, dd, J=8.4, 10.0Hz), 7.65-7.67 (1H, m), 7.78(1H, s), 7,85 (1H, brs) MS (ESI) : M+ 392

The synthetic route of 2-Fluoro-5-iodobenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Tobacco Inc.; EP1564210; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 619-58-9, A common heterocyclic compound, 619-58-9, name is 4-Iodobenzoic acid, molecular formula is C7H5IO2, 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-iodobenzoic acid (6 g, 24.19 mmol) in DCM (300 mL) was added 1,1-carbonyldiimidazole (4.3 15 g, 26.61 mmol) at0C. After being stirred at rt for 2h, hydrazine monohydrate (7.26 g, 145.15 mmol) was added and the mixture was stirred at ft for 5h. The mixture was then concentrated under reduced pressure followed by the addition of water to precipitate out the product. The product was collected by filtration and dried under reduced pressure to afford 15-1 (5.2 g, 82%) as an off white solid. LCMS: 263.05 [M+Hjt

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; KALYRA PHARMACEUTICALS, INC.; HUANG, Peter, Qinhua; KAHRAMAN, Mehmet; BUNKER, Kevin, Duane; (194 pag.)WO2018/67512; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 19718-49-1, 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. 19718-49-1, name is Methyl 4-amino-3-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A flask was charged with methyl 4-amino-3-iodobenzoate (7.50 g, 27.1 mmol, 1.00 equiv), DCM (50 mL), triethylamine (7.20 g, 71.3 mmol, 2.63 equiv) and trifluoroacetic anhydride (8.90 g, 42.4 mmol, 1.57 equiv), as described in Example 1, Step 1. The residue was chromatographed on a silica gel column to provide 8.00 g (79% yield) of methyl 3-iodo-4- (2,2,2-trifluoroacetamido)benzoate as a yellow solid.

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 4-amino-3-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WEBER, Olivia D.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; JONES, Todd K.; (275 pag.)WO2019/46318; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 460-37-7, 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. 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

6-Ch[oro-N-(piperidin-4-y[)pyrazine-2-carboxamide trifluoroacetic acid salt[Intermediate 65] (1 .49 g, 6.20 mmol, 1 .0 eq), and potassium carbonate (4.28 g, 31.0 mmol, 5.0 eq) were suspended in 33 mL acetonitrile. Then, 1,1,1- trifluoro-3-iodopropane [CAS RN: 460-37-7] (2.08 g, 9.30 mmol, 1.5 eq) was added and the reaction mixture was heated to 70C for 4 h. On cooling, the reaction mixture was diluted with water and extracted withdichloromethane/isopropanol (4/1) (2x). The combined organic phases were washed with brine. Phase separation was conducted by the use of a Whatman filter. The volatile components were removed in vacuo and the crude material was purified via preparative MPLC (Biotage Isolera; 50 g SNAP cartridge:dichloromethane -> dichloromethane/ethanol 95/5) to give 900 mg (41% yield oftheory) of the title compound.UPLC-MS (Method 1): R = 0.56 mm; MS (ESI0): m/z = 337 [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, 1,1,1-Trifluoro-3-iodopropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 624-75-9,Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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: Starting amine (5.0 mmol) was dissolved in dry diethyl ether (17 mL) and iodoacetonitrile (5.5 mmol, 919 mg) was added dropwise under cooling. The mixture was stirred at room temperature for 3-14 days, then precipitate was filtered off, washed with diethyl ether and dried in vacuo to give the corresponding quaternary ammonium salt 2. If the solid precipitate was not formed after 7 days, the mixture was evaporated under reduced pressure. The crude product was washed with diethyl ether (3 × 15mL) and dried in vacuo. The quaternary ammonium salt 2 was used in the next step without additional purification. The corresponding quaternary ammonium salt (3.0 mmol) was heated at 150 C on oil bath in freshly distilled DMF (7 mL) in a 25 mL round-bottom flask fitted with reflux condenser and CaCl2-tube for 15 minutes. The mixture was cooled to room temperature, diluted with H2O (20 mL) and extracted with PhMe (2 × 15mL). The organic phase then was washed with H2O (2 × 15mL) and brine (15 mL), dried over Na2SO4 and evaporated in vacuo to give the desired aminoacetonitrile 4. The latter, if necessary, was purified by column chromatography (it is convenient to visualize aminoacetonitriles on TLC-plate by treating with the diluted solution of ninhydrin in EtOH). Note, that aminoacetonitriles are moisture sensitive. Products after column chromatography were additionally dried by the addition of dry PhMe (5 mL) and evaporation in vacuo.

The synthetic route of 624-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Buev, Evgeny M.; Smorodina, Anastasia A.; Stepanov, Maxim A.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Y.; Tetrahedron Letters; vol. 59; 17; (2018); p. 1638 – 1641;,
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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 101335-11-9

To a solution of 2-chloro-4-fluoroiodobenzene (11.6 g) in THF (80 mL) was added dropwise isopropylmagnesium chloride-lithium chloride complex (1.3M THF solution, 34.8 mL) over 20 min at -78 C., and the mixture was stirred at -15 C. for 1.5 hr. To this mixture was added tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (6.16 g), and the mixture was stirred at room temperature for 48 hr. The reaction was quenched with aqueous ammonium chloride solution at 0 C., and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.41 g). 1H NMR (300 MHz, CDCl3) delta1.46 (9H, s), 1.54-1.71 (2H, m), 1.79-1.94 (2H, m), 2.72-2.94 (2H, m), 3.17-3.31 (1H, m), 4.01-4.19 (2H, m), 7.01-7.09 (1H, m), 7.17 (1H, dd, J=8.5, 2.5 Hz), 7.39 (1H, dd, J=8.6, 5.9 Hz).

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 101335-11-9.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Ikeda, Shuhei; SUGIYAMA, Hideyuki; AIDA, Jumpei; TOKUHARA, Hidekazu; OKAWA, Tomohiro; OGURO, Yuya; NAKAMURA, Minoru; MURAKAMI, Masataka; (71 pag.)US2017/283406; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com