Month: August 2021

Electric Literature of 103440-52-4,Some common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, molecular formula is C9H9IO2, 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: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuI (10 mg, 0.05 mmol, 10 mol%), K2CO3 (276 mg, 2.0 mmol), 1,10-phenanthroline (20 mg, 0.10 mmol, 20 mol%) and cyclic thiourea (0.5 mmol), 4 ? Molecular Sieves. The tube was evacuated and backfilled with N2 (this procedure was repeated 3 times). Under a counter flow of N2, methyl-2-iodobenzoate 1 (0.6 mmol) and DMF (2.0 mL) were added by syringe. The mixture was stirred at 100 ºC for 24h. After the reaction was completed, the mixture was directly passed through celite and rinsed with 30 mL of EtOAc. The combined filtrate was concentrated and purified by column chromatography on silica gel to give the pure product.Yellow Yellow solid; mp 126-128 C; 1H NMR (400 MHz, CDCl3) delta 8.04 (s, 1H), 7.31 (d, J = 7.6 Hz,1H), 7.12 (d, J = 8.0 Hz,1H), 3.52-3.45 (m, 1H), 3.28-3.22 (m, 1H), 3.12-3.09 (m, 1H), 2.38-2.36 (m, 4H), 1.91 (s, 2H), 1.72-1.63 (m, 1H), 1.56-1.43 (m, 3H); 13C NMR (50 MHz, CDCl3) delta 162.5, 154.8, 137.0, 134.5, 130.9, 128.6, 125.2, 124.5, 71.7, 67.5, 31.1, 30.9, 25.4, 25.0, 21.1 ppm. Anal. Calcd. for C15H16N2OS: C 66.15, H 5.92, N 10.29; found: C 66.21, H 5.70, N 10.37; EI-MS: m/z = 272 (M+).

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

Reference:
Article; Chen, Dingben; Wu, Jiashou; Yang, Jianguo; Huang, Ling; Xiang, Yubo; Bao, Weiliang; Tetrahedron Letters; vol. 53; 52; (2012); p. 7104 – 7107;,
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Application of 13421-00-6, 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. 13421-00-6, name is 5-Chloro-2-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of N-((4-(trifluoromethyl)cyclohexyl)methyl)propan-2-amine (250 mg, 1.07 mmol) in DMF (4 mL) was added 5-chloro-2-iodobenzoic acid (395 mg, 1.4 mmol), HATU (610 mg, 1.6 mmol) and DIEA (480 muL, 2.7 mmol). The mixture was stirred at rt for 3 h. Ethyl acetate (10 mL) and water (10 mL) were added to the mixture. After partition, the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The solvent was removed in vacuo to give the crude product which was purified by flash chromatography over silica gel (eluting with 15% EtOAc in hexanes) to afford 420 mg of 5-chloro-2-iodo-N-isopropyl-N-((4-(trifluoromethyl)cyclohexyl)methyl)benzamide as a clear oil (86% yield). LC-MS tR=1.99 min in 2 min chromatography, MS (ESI) m/z 488.2 [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, 5-Chloro-2-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; Claremon, David A.; Dillard, Lawrence Wayne; Dong, Chengguo; Fan, Yi; Jia, Lanqi; Lotesta, Stephen D.; Marcus, Andrew; Singh, Suresh B.; Tice, Colin M.; Yuan, Jing; Zhao, Wei; Zheng, Yajun; Zhuang, Linghang; (65 pag.)US2016/122318; (2016); A1;,
Iodide – Wikipedia,
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Related Products of 25245-29-8,Some common heterocyclic compound, 25245-29-8, name is 5-Iodo-1,2,3-trimethoxybenzene, molecular formula is C9H11IO3, 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 2.36 g (8.0 mmol) of 1-iodo-3,4,5-trimethoxybenzene(2) in triethylamine (80 ml) were added 1.38 ml (9.6 mmol) of 3,3-diethoxy-1-propane, 56 mg (0.080 mmol) of bis(triphenylphosphine)palladium (II) chloride and 8.0 mg (0.040 mmol) of cuprous iodide with stirring under nitrogen, and the mixture was stirred for 3 hours at room temperature. Insoluble materials were removed from the reaction mixture by suction filtration through Celite, and the filtrate was concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel to obtain 2.29 g (yield: 97%) of 1,1-diethoxy-3-(3,4,5-trimethoxyphenyl)-2-propyne as colorless needles (melting point: 62.5-63.0 C.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Iodo-1,2,3-trimethoxybenzene, its application will become more common.

Reference:
Patent; Kowa Co., Ltd.; US6340682; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, 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 19094-56-5, Quality Control of 2-Chloro-5-iodobenzoic acid

Preparation 2-Chloro-5-iodo-N-(tricyclo[3.3.1.13’7]dec- 1 -ylmethyD-benzamide (Compound A); 5-Iodo-2-chlorobenzoic acid (40.0Og, 141.6mmol) was charged to a 500ml reaction vessel, followed by Bu4NCl (0.4Og, O.Oleq, 1.42mmol) and toluene (80ml, 2vol) under an inert atmosphere (N2). The suspension was heated to 70-75C, then thionyl chloride (12.40ml, 1.2eq, 169.94mmol) was added drop-wise over 30-60min. The resulting suspension is heated at 70-750C for approximately 3 hours. The reaction was monitored by HPLC (MeOH quench of sample) and on completion the reaction mixture, now a clear solution of 5-iodo-2-chlorobenzoyl chloride, was cooled to 20-250C

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

Reference:
Patent; ASTRAZENECA AB; WO2008/30160; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 19094-56-5, 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. 19094-56-5, name is 2-Chloro-5-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred suspension of 2-chloro-5-iodobenzoic acid(5.65 g, 0.02 mol) in CH2Cl2(20 mL) was added oxalylchloride(1.80 mL, 0.021 mol) and DMF(0.02 mL). Theresulting mixture was stirred for 4 h at room temperature.The mixture was concentrated, and the residual colorlesssolid was dissolved in CH2Cl2(40 mL). To this solutionwere added corresponding substituted benzene(0.02 mol)and then AlCl3(2.75 g, 0.021 mol) portionwise so that thetemperature did not exceed 0 C. After being stirred at 10-20 C for 3 h, the mixture was poured into ice water andextracted with CH2Cl2 three times. The combined organiclayers were washed with 1M HCl, water, and brine, thendried over MgSO4 and concentrated. The residual solid wascrystallized from ethanol to give as white solid.According to this procedure the following compoundswere prepared.

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

Reference:
Article; Hu, Shengquan; Sun, Wuji; Wang, Yeming; Yan, Hong; Medicinal Chemistry Research; vol. 28; 4; (2019); p. 465 – 472;,
Iodide – Wikipedia,
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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 461-17-6 as follows. Product Details of 461-17-6

[00106] To a solutiion of 6-bromo-benzo[cd]indol-2(1H)-one (1 g, 4 mmol) in N,N-dimethyl formamide was added K2CO3 (5.53 g, 40 mmol) and the resulting mixture was stirred for 0.5 hour under nitrogen. 4,4,4-trifluorobutyl iodide (915 mg, 4 mmol ) was next injected to the solution and the mixture was heated at 60 C. for 18 hours. The reaction media was next poured into 200 ml water and extracted with trichloromethane (3×100 ml). Column chromatography using gradient ethyl acetate in hexane (1020%) gave the desired product (1.225 g, 85%).

According to the analysis of related databases, 461-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US6667303; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 1829-28-3,Some common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, 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: Hydrazides (30?58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3?6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).

The synthetic route of 1829-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mehr-Un-Nisa; Munawar, Munawar A.; Chattha, Fauzia A.; Kousar, Samina; Munir, Jawaria; Ismail, Tayaba; Ashraf, Muhammad; Khan, Misbahul A.; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 6014 – 6024;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 328-73-4, 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. 328-73-4, name is 1-Iodo-3,5-bis(trifluoromethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.

The synthetic route of 1-Iodo-3,5-bis(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 68; 24; (2012); p. 4701 – 4709;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 886762-71-6, 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. 886762-71-6, name is 1-Fluoro-3-iodo-2-nitrobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Potassium tert-butoxide (92 mg, 0.824 mmol) was added portionwise over 5 mm to a solution of 1-fluoro-3-iodo-2-nitrobenzene (200 mg, 0.749 mmol) and EtOH (0.052 mL, 0.90 mmol) intoluene (3 mL), then the mixture was stirred at RT for 2 h. FCC (toluene) afforded the title compound as a colourless solid (247 mg, assume quantitative). ?H NMR (CDC13) oe 7.41 (1H, d), 7.10 (1H, t), 7.00 (1H, d), 4.13 (2H, q), 1.40 (3H, t).

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-Fluoro-3-iodo-2-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ANTABIO SAS; LEIRIS, Simon; DAVIES, David Thomas; EVERETT, Martin; SPRYNSKI, Nicolas; SUTTON, Jonathan Mark; BODNARCHUK, Michael Steven; PALLIN, Thomas David; CRIDLAND, Andrew Peter; BLENCH, Toby Jonathan; CLARK, David Edward; ELLIOTT, Richard Leonard; (197 pag.)WO2018/172423; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 202982-67-0,Some common heterocyclic compound, 202982-67-0, name is 4-Chloro-3-fluoroiodobenzene, molecular formula is C6H3ClFI, 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.

A mixture of Example 47C (62 mg, 0.151 mmol), l-chloro-2-fluoro-4-iodobenzene (40.7 mg, 0.159 mmol) and cesium carbonate (148 mg, 0.454 mmol) in dioxane (2.0 mL) was bubbled with argon for 5 minutes and treated with dicyclohexyl(2′,4′,6′-triisopropyl-[l,l’-biphenyl]-2- yl)phosphine (10.82 mg, 0.023 mmol) and Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(O)) (11.08 mg, 0.012 mmol). The reaction mixture was flushed with argon for an additional five minutes and stirred at 95 C for 1 hour. After cooling, the reaction mixture was treated with sodium tetrahydroborate (11.45 mg, 0.303 mmol) and stirred for 2 hours. Volatiles were removed, and the residue was purified by HPLC (20-100% acetonitrile in 0.1% trifluoroacetic acid/water on Phenonemex CI 8 10 muiotaeta column) twice to provide the title compound (33mg, 40%). H NMR (400 MHz, DMSO-d6) delta ppm 7.71 (dd, J = 12.8, 2.5 Hz, 1H), 7.48 (td, J = 8.8, 4.8 Hz, 2H), 7.29 (s, 1H), 7.33 – 7.12 (m, 1H), 7.06 (dd, J = 11.4, 2.9 Hz, 1H), 6.84 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 5.13 (s, 1H), 4.48 (s, 2H), 4.13 – 4.05 (m, 1H), 3.67 (dd, J = 9.2, 6.5 Hz, 2H), 3.45 (dd, J = 9.1, 6.6 Hz, 2H), 2.39 (ddd, J = 12.5, 9.4, 2.5 Hz, 1H), 2.16 – 2.00 (m, 2H), 2.03 – 1.73 (m, 7H); MS (ESI+) m/z 540.2 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-fluoroiodobenzene, its application will become more common.

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; SHI, Lei; CHUNG, Seungwon; XIONG, Zhaoming; MURAUSKI, Kathleen; ZHANG, Qingwei, I.; BROWN, Brian, S.; DART, Michael, J.; (267 pag.)WO2019/90081; (2019); A1;,
Iodide – Wikipedia,
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