Tag: M.W=200-300

Synthetic Route of 7425-53-8,Some common heterocyclic compound, 7425-53-8, name is Ethyl 4-iodobutanoate, molecular formula is C6H11IO2, 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.

; As a starting material for obtaining the compound of the formula (4), starting from the compound 1 as in Synthetic Example 1, the compound 11 was prepared via the compound 9 and the compound 10. [Show Image] [Show Image] [Show Image] First, conversion of ethyl 4-bromobutyrate into ethyl 4-iodobutyrate was carried out. Into 250 ml of acetone was dissolved 34.2 g (175 mmol) of ethyl 4-bromobutyrate, and then 29.1 g (175 mmol) of potassium iodide was added thereto, followed by heating under reflux over a period of 20 hours. Then, after the reaction solution was allowed to cool to room temperature, the solvent was removed by distillation and the residue was extracted with 150 ml of ethyl acetate. The resulting organic layer was washed with 50 ml of distilled water and then dried over anhydrous magnesium sulfate. Then, 43.2 g of a crude product was obtained by removing the solvent by distillation and drying under reduced pressure. As a result of 1H-NMR analysis, it was found that the crude product contained ethyl 4-iodobutyrate in a molar fraction of 92%. The crude product was used in the following step as it was. Next, 30.5 g (155 mmol) of the compound 1 was dissolved in 450 ml of tetrahydrofuran, and the resulting solution was cooled to -78C with dry ice/acetone. To the resulting solution was dropwise added 100 ml (156 mmol) of 1.56 M n-butyllithium/n-hexane solution. After the resulting mixture was stirred at the same temperature for 45 minutes, a solution of the crude product of ethyl 4-iodobutyrate, which had been prepared as above and dissolved in 50 ml of tetrahydrofuran, was dropwise added to the mixture. After dropwise addition, the resulting mixture was stirred at the same temperature for 10 minutes and then, the temperature was gradually elevated. When the temperature of the reaction solution reached -10C, 50 ml of 5% citric acid aqueous solution was added to terminate the reaction. To the reaction mixture were added 100 ml of 10% sodium thiosulfate aqueous solution, 150 ml of saturated sodium chloride aqueous solution, and 50 ml of ethyl acetate, followed by partitioning. The organic layer was separated and the aqueous layer was extracted in 50 ml of ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation and purification by silica gel column chromatography was carried out to obtain 46.0 g (yield 96%) of a pale yellow, liquid compound having a low viscosity. The chemical shift values of the product on 1H-NMR spectrum as measured in deuterochloroform were as follows: 1.23 (3H, t), 1.52-1.63 (1H, m), 1.65-1.80 (2H, m), 2.07-2.15 (1H, m), 2.25-2.37 (2H, m), 2.44 (3H, s), 3.45-3.55 (1H, m), 4.10 (2H, q), 5.08 (1H, d), 5.31 (1H, d), 5.57-5.66 (1H, m), 7.32 (2H, d), 7.70 (2H, d). The wave numbers (cm-1) with absorption on IR absorption spectrum (KBr pellet method) were as follows: 2980, 2930, 1730, 1600, 1300, 1290, 1140, 1090, 820, 670. The results of elemental analysis were as follows: carbon 61.73% and hydrogen 6.92%. Based on the above analysis, it was confirmed that the obtained compound was the compound 9. Next, conversion from the compound 9 to the compound 10 was carried out. Into 360 ml of tetrahydrofuran and 120 ml of methanol was dissolved 46.0 g (148 mmol) of the compound 9, and 3.42 g (2.96 mmol) of tetrakistriphenylphosphine palladium was added. The reaction solution was heated under reflux over a period of 16 hours. Then, after the reaction solution was allowed to cool to room temperature, the solvent was removed by distillation and purification by silica gel chromatography was carried out to obtain 41.0 g (89%) of a pale brown, liquid compound having a low viscosity. As a result of 1H-NMR analysis, IR absorption spectrum analysis, and elemental analysis shown below, it was confirmed that the product contained the compound 10 in a molar fraction of 81% and the remaining 19% was a geometrical isomer wherein the carbon-carbon double bond in the compound 10 was arranged in a cis-form. The chemical shift values of the compound 10 on 1H-NMR spectrum as measured in deuterochloroform were as follows: 1.25 (3H, t), 1.57-1.65 (2H, m), 2.03-2.10 (2H, m), 2.20 (2H, t), 2.44 (3H, s), 3.73 (2H, d), 4.12 (2H, q), 5.37-5.55 (2H, m), 7.33 (2H, d), 7.73 (2H, d). The wave numbers (cm-1) with absorption on IR absorption spectrum (KBr pellet method) were as follows: 2980, 2930, 1730, 1600, 1320, 1300, 1150, 1090, 820, 740. The results of elemental analysis were as follows: carbon 61.81% and hydrogen 7.01%. The compound 11 was prepared from the compound 10. A solution of 6.63 g (21.4 mmol) of the compound 10 dissolved in 65 ml of tetrahydrofuran was cooled to -78C with dry ice/acetone. To the solution was dropwise added 11.0 ml (22.0 mmol) of 2.0 M lithium diisopropylamide/heptane-tetrahydrofuran-ethylbenzene solution. After the resulting mixture was stirred at the same temperature for 60 minutes, a solution of 6.09 g (2…

The synthetic route of 7425-53-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOAGOSEI CO., LTD.; EP1612201; (2006); A1;,
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Reference of 123158-75-8, These common heterocyclic compound, 123158-75-8, name is 4-Chloro-2-iodo-6-nitroaniline, 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.

2-Amino-5-chloro-3-nitro-phenyliodide (1.5 g, 4.90 mmol) prepared in Preparation 19 and l-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 rnL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100C . After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%). 1H-NMR (400HMz, CDCl3); delta 9.78(br s, IH), 8.15(s, IH), 7.78(s, IH),7.38~7.48(m, 5H), 0.26(s, 9H)

The synthetic route of 123158-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG LIFE SCIENCES LTD.; WO2009/25478; (2009); A1;,
Iodide – Wikipedia,
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5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 5471-81-8

DMF (110 mL) was added to 4-iodo-3-methylbenzoic acid methyl ester (3.16 g), methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (14.5 mL), and copper(I) iodide (2.18 g), and the mixture was stirred with heating at 90C for 4 hours. The reaction mixture was cooled to room temperature, and saturated brine was added thereto. The mixture was extracted thrice, each with ethyl acetate, and the extracts were combined. The combined extract was washed with saturated brine, and dried over sodium sulfate. Insoluble matter was removed by filtration, and then the filtrate was concentrated. The residue was purified by silica gel column chromatography, whereby the title compound (2.66 g) was yielded. 1H-NMR (CDCl3) delta : 2.56(3H,s), 3.95(3H,s), 7.68(1H,d, J=8.1Hz), 7.93(1H,d,J=8.1Hz),7 .96 (1H, s).

The synthetic route of 5471-81-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2017263; (2009); A1;,
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1878-69-9, name is 2-(3-Iodophenyl)acetic acid, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8H7IO2

EXAMPLE A.4. Compound c-3 (127l): 4-(4-fluoro-3-(4-(2-(3-iodophenyl)acetyl)piperazine-l-carbonyl)- benzyl)phthalazin-l(2H)-one. A solution of 3-iodophenyl acetic acid (6.5 mg, 0.048 mmol), l-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) (10.5 mg, 0.055 mmol), N-hydroxy succinimide (NHS) and 600 mu DM F was stirred for 30 min at room temperature. Then, 4-(4-fluoro-3-(piperazine-l-carbonyl)benzyl)- phthalazin-l(2H)-one (10 mg, 0.0275 mmol) was added to the solution and the mixture was stirred at room temperature overnight. The reaction was washed with 500 mu of H20 and extracted with 500 mu dichloromethane (DCM). The resulting organic solution was purified on silica gel, using a gradient elution from neat DCM to DCM/hexane 5:1 to obtain the desired product as a white solid (3 mg, 20% yield). 1H NMR (CDCI3) delta = 9,82 (s, 1H), 8.40-8.38 (m, 1H), 7.71-7.69 (m, 2H), 7.55-7.53 (m, 1H), 7.51-7.50 (m, 2H), 7.25-7.24 (m, 2H), 7.09-6.90 (m, 3H), 4.20 (s, 2H), 3.64-3.31 (m, 8H), 2.84 (s, 2H). LC-ESI-MS (+) m/z = 633.1 [M+Na+]+. HRMS-ESI [M+H+]+ m/z calculated for [C28H24FIN403]+ 611.0955, found 611.0948.

The synthetic route of 1878-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORIAL SLOAN KETTERING CANCER CENTER; REINER, Thomas; LEWIS, Jason S.; WEBER, Wolfgang; RODRIGUEZ, Beatriz Salinas; CARNEY, Brandon; CARLUCCI, Giuseppe; (89 pag.)WO2016/33293; (2016); A1;,
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Related Products of 401-81-0, 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. 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a resealable Schlenk tube, was added Cs2CO3 (2.0mmol), KSCN (1.5mmol) and MCM-41-2N-CuCl (110mg, 0.05mmol), and the reaction vessel was fitted with a rubber septum. The vessel was evacuated and back-filled with argon and this evacuation/back-fill procedure was repeated one additional time. The aryl iodide (1.0mmol) and water (3mL) were then added under a stream of argon. The reaction tube was quickly sealed and the contents were stirred while heating in an oil bath at 130C for 48h. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with ethyl acetate (3¡Á5mL), and filtered. The MCM-41-2N-CuCl complex was washed with distilled water (2¡Á5mL), ethyl acetate (2¡Á5mL), and Et2O (2¡Á5mL) and reused in the next run. The extract was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (petroleum/ethyl acetate=50:1 to 10:1) to provide the desired product.

The synthetic route of 1-Iodo-3-(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Short Survey; Cai, Mingzhong; Xiao, Ruian; Yan, Tao; Zhao, Hong; Journal of Organometallic Chemistry; vol. 749; (2014); p. 55 – 60;,
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Reference of 61272-76-2, 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. 61272-76-2, name is 4-Fluoro-2-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 2-iodoaniline (0.5 mmol), CS2 (0.6 mmol), an amine (0.6 mmol), CuO nanoparticles (0.5 mmol), and KOH (1.5-2 mmol) in DMSO (3 mL) was stirred at 110 ¡ãC for 6 h. The cooled solution was partitioned between ethyl acetate and water, and the organic layer was washed with water and brine, and then dried over Na2SO4. After removal of the solvent in vacuo, the residue was purified by silica-gel chromatography to give the desired benzothiazole.

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-2-iodoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Satish; Reddy, K. Harsha Vardhan; Ramesh; Karnakar; Nageswar; Tetrahedron Letters; vol. 53; 20; (2012); p. 2518 – 2521;,
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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. Recommanded Product: 460-37-7

Example 182Preparation of 4-((lR,3aS,5aR,5bR,7aR,llaS,llbR,13aR,13bR)-5a,5b,8,8,lla- pentamethyl-l-(prop-l-en-2-yl)-3a-((3,3,3-trifluoropropyl)amino)- 2,3,3a,4,5,5a,5b,6,7,7a,8,ll,lla,llb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoic acidStep 1. Preparation of methyl 4-((lR,3aS,5aR,5bR,7aR, l laS, l lbR, 13aR, 13bR)- 5a,5b,8,8, 1 1 a-pentamethyl- 1 -(prop- 1 -en-2-yl)-3 a-((3,3 ,3 -trifluoropropyl)amino)- 2,3,3a,4,5,5a,5b,6,7,7a,8, l l, l la, l lb, 12, 13, 13a, 13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate.To a sealable vial containing methyl 4-((lR,3aS,5aR,5bR,7aR, l laS,l lbR, 13aR, 13bR)-3a-amino-5a,5b,8,8, l la-pentamethyl- 1 -(prop- 1 -en-2-yl)-2,3,3 a,4,5,5a,5b,6,7,7a,8, 11 , 11 a, 1 lb, 12, 13, 13 a, 13b- octadecahydro-lH-cyclopenta[a]chrysen-9-yl)benzoate, HC1 (0.075 g, 0.129 mmol) was added potassium carbonate (0.036 g, 0.258 mmol). The mixture was diluted with DMF (1 mL) and l-iodo-3,3,3-trifluoropropane (0.045 mL, 0.388 mmol) was added. The vial was sealed and the mixture was heated to 75 C for 23h then was cooled to rt. LC/MS showed a mixture of starting material and product. An additional 0.045 mL of l-Iodo-3,3,3-trifluoropropane was added and the mixture and was heated to 75 C for 48h then was cooled to rt. LC/MS showed further progression, but the reaction was still not complete. An additional 0.045 mL of l-iodo-3,3,3-trifluoropropane was added and the mixture was heated to 75 C for 71h, then was cooled to rt and was concentrated under reduced pressure. The mixture was adsorbed to silica gel and was purified by flash chromatography using a 0-15% EtOAc in hexanes gradient with 0.1% ammonium hydroxide added to the mixture and a Thomson 12g silica gel column. The fractions containing the expected product were combined and were concentrated under reduced pressure to give methyl 4-((lR,3aS,5aR,5bR,7aR, l laS, l lbR, 13aR, 13bR)-5a,5b,8,8, l la-pentamethyl-l-(prop-l- en-2-yl)-3a-((3,3,3-trifluoropropyl)amino)-2,3,3a,4,5,5a,5b,6,7,7a,8, l l, l la, l lb, 12, 13, 13a, 13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate (0.032 g, 0.044 mmol, 34.1 % yield) as a white foam. LCMS: m/e 640.6 (M+H)+, 2.15 min (method 2). XH NMR (500 MHz, chloroform-d) delta 7.92 (d, J=8.24 Hz, 2H), 7.19 (d, J=8.24 Hz, 2H), 5.28 (dd, J=1.53, 6.10 Hz, 1H), 4.70 (d, J=1.83 Hz, 1H), 4.59 (s, 1H), 3.90 (s, 3H), 2.60-2.73 (m, 2H), 2.56 (dt, J=5.34, 10.91 Hz, 1H), 2.21-2.32 (m, 2H), 2.09 (dd, J=6.41, 17.09 Hz, 1H), 1.68 (s, 3H), 1.07 (s, 3H), 0.98 (s, 6H), 0.92 (s, 3H), 0.92 (br. s., 3H), 0.84-2.01 (m, 21H).

The synthetic route of 460-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; REGUEIRO-REN, Alicia; LIU, Zheng; SWIDORSKI, Jacob; SIN, Ny; VENABLES, Brian Lee; SIT, Sing-Yuen; CHEN, Yan; CHEN, Jie; MEANWELL, Nicholas A.; WO2012/106190; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 161949-50-4, name is 2-Chloro-5-iodoanisole, 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 161949-50-4, name: 2-Chloro-5-iodoanisole

2nd reaction step: 4-Chloro-3-methoxybenzeneboronic acid In a flame-dried flask, 1.93 g (79.2 mmol) of magnesium turnings were etched with a small crystal of iodine, and 50 ml of anhydrous ether were added. Then, under a nitrogen atmosphere, a solution of 20.0 g (79.2 mmol) 2-chloro-5-iodoanisole in 50 ml of anhydrous ether were added dropwise in such a way that the ether was kept boiling by the heat of reaction. After the addition was complete, the mixture was refluxed for 11/2 hours and then filtered through glass wool, with exclusion of moisture, into a dropping funnel. This Grignard solution and, synchronously but separately, 8.24 g (79.2 mmol) of trimethyl borate were added dropwise to 50 ml of anhydrous ether in a flame-dried flask under a nitrogen atmosphere at -60 to -70 C. The resulting suspension was then stirred at the stated temperature for one hour and, after it had warmed to about 20 C., acidified to pH 3 with 5% strength sulfuric acid. After separation of the phases, the aqueous phase was extracted three times with ether. The combined organic phases were dried over sodium sulfate and then concentrated. The residue was extracted by boiling three times with 100 ml of water each time. The aqueous phases were combined and cooled, when 4.6 g (32%) of colorless crystals separated out and were removed and dried under reduced pressure at 20-25 C. 1 H-NMR (270 MHz, in d6 -DMSO): delta [ppm]=3.90(s,3H), 7.39(s,2H), 7.56(s,1H), 8.2(s,br.,2H).

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-Chloro-5-iodoanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF Aktiengesellschaft; US5783522; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 4028-63-1, A common heterocyclic compound, 4028-63-1, name is 2,4,6-Trimethyliodobenzene, molecular formula is C9H11I, 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: A 10 mL flask equipped with a Teflon valve was charged with a magnetic stir bar, CuI (2 mg, 1molpercent), Heteroarylamine (1.5 mmol), KOtBu (224 mg, 2.0 mmol), solid aryl halides (1.0 mmol). The tube was evacuated and backfilled with argon. Under a counter flow of argon, dioxane (1.5mL), aryl halides (1.0 mmol, if liquid) were added by syringe. The tube was sealed. The reaction mixture was allowed to stir at 110 ¡ãC (X=I) or 130 ¡ãC (X= Br) for 24 h. Then the mixture was cooled to room temperature and added 5.0 mL brine. Subsequently, the mixture was extracted with ethyl acetate. The organic layers were collected, dried over Na2SO4, filtered and the solvent was removed under vacuum. The residue was purified by column chromatography on silica gel.

The synthetic route of 4028-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Deping; Kuang, Daizhi; Zhang, Fuxing; Liu, Yang; Ning, Shunhua; Tetrahedron Letters; vol. 55; 51; (2014); p. 7121 – 7123;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 61272-76-2, 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. 61272-76-2, name is 4-Fluoro-2-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 2-Iodoaniline 2a (65.7 mg, 0.3 mmol), Cu(OAc)2 (6 mg, 10percent), KOtBu (101 mg, 0.9 mmol), DMAc (1.0 mL) were mixed in a Schlenck tube and then to the mixture was added 2-(phenylethynyl)benzonitrile1a (74 mg, 0.36 mmol) under N2. The reaction mixture was stirred for 12 h at 120 ¡ãC under N2. After the reaction was completed (monitored by TLC), the reaction mixture was then diluted with water and extracted with ethyl acetate. After the combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure, the residue was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate as eluent to afford the pure product 3

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-2-iodoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
Iodide – Wikipedia,
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