Month: August 2021

Electric Literature of 90347-66-3, A common heterocyclic compound, 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, molecular formula is C9H9IO2, 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 round-bottom flask containing 3-iodo-4-methyl-benzoic acid methyl ester (1.38 g, 5.00 mmol), 4-cyanophenylboronic acid (1.10 g, 7.48 mmol), palladium acetate (168 mg, 0.748 mmol), 2-(dicyclohexylphosphino)biphenyl (0.526 g, 1.50 mmol) and potassium fluoride (0.870 g, 15.0 mmol) is added anhydrous 1,4-dioxane (15 ml). The flask is purged with argon and sealed. The mixture is stirred at 130 C. for 18 hours, cooled to ambient temperature and then water (20 ml) and ethyl acetate (20 ml) are added. Solid is removed under vacuum filtration. The filtrate is extracted with EtOAc (20 ml×2). The organic layers are combined, washed with aqueous HCl (5%, 20 ml) and saturated NaHCO3 (20 ml). It is dried over MgSO4, and concentrated. The residue is purified by silica gel column chromatography (EtOAc/Hexane, gradient) to give 4′-cyano-6-methyl-biphenyl-3-carboxylic acid methyl ester 2; LC-MS m/z: 252.1 (M+1).

The synthetic route of 90347-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; US2009/203666; (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. 444-29-1, name is 1-Iodo-2-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H4F3I

To a solution of 7-ethynyl-2,2-dimethyl-2,3-dihydro-4H-pyrano[2,3-b]pyridin-4-one 29 (0.25 g, 1.23 mmol) in DMSO (3.0 mL) was added copper(I) iodide (0.005 g, 0.026 mmol), dichlorobis(triphenyl- phosphine)palladium (II) (0.034 g, 0.37 mmol), triethylamine (1.0 mL), 1-iodo-2-(trifluoromethyl)- benzene (0.505 g, 1.85 mmol). The reaction mixture was further stirred at 100 °C for 4 h. After the completion of reaction, the reaction mixture was filtered through celite bed. The filtrate was quenched with water, extracted with ethyl acetate and concentrated. The crude compound was purified by flash chromatography using 10-20percent ethyl acetate in hexane to provide title compound 30a (0.2 g) in 46percent yield. 1H NMR (CDCl3): delta 1.54 (s, 6H), 2.80 (s, 2H), 7.27 (s, 1H), 7.48 (d, J = 7.80 Hz, 1H), 7.58 (d, J = 6.9 Hz, 1H), 7.73 (t, J = 7.8 Hz, 2H), 8.20 (d, J = 7.8 Hz, 1H); MS [M+H]+: 346.14.

The synthetic route of 444-29-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Muthukaman, Nagarajan; Tambe, Macchindra; Shaikh, Mahamadhanif; Pisal, Dnyandeo; Deshmukh, Sanjay; Tondlekar, Shital; Sarode, Neelam; Narayana, Lakshminarayana; Gajera, Jitendra M.; Kattige, Vidya G.; Honnegowda, Srinivasa; Karande, Vikas; Kulkarni, Abhay; Behera, Dayanidhi; Jadhav, Satyawan B.; Gudi, Girish S.; Khairatkar-Joshi, Neelima; Gharat, Laxmikant A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 11; (2017); p. 2594 – 2601;,
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 6828-35-9 as follows. SDS of cas: 6828-35-9

The corresponding imidazopyridine (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.Cuprous iodide (0.03 mmol), 2-iodo-5-chloroaniline (0.4 mmol),1,10-azaphenanthroline (0.04 mmol), DBU (0.6 mmol),Carbon disulfide (0.8 mmol) and toluene (2.0 mL) were added by syringe under oxygen.The reaction tube was placed in a 120 C oil bath and stirred for 12 hours.The resulting solution was cooled to room temperature, and 2 mL of deionized water was added to the reaction solution.Mix well, each time with 3mL of ethyl acetate as extractant through liquid separation extraction operation,The crude product is extracted from the reaction solution, and the extract is combined.The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (silica gel, 200 to 300 mesh, eluent, petroleum ether / ethyl acetate (8:1 v/v)).The target product was obtained 66.8 mg, yield 82%.

According to the analysis of related databases, 6828-35-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (2019); A;,
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

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

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

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 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

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

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