Tag: M.W=200-300

Synthetic Route of 52548-14-8,Some common heterocyclic compound, 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, 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.

Add 1.1 kg of acetone to the 5L reaction flask.131g 2-iodo-5-methylbenzoic acid,Stir and dissolve,Add 350g of anhydrous potassium carbonate,After heating to reflux (55-60 C) for half an hour, add 114g 1,2,3-triazole,2.4 g of cuprous iodide.The reaction was kept under reflux (55-60 C) for 8 hours, sampled, and sampled once every 1 h. After the reaction was completed, it was cooled to room temperature for filtration, and the filter cake was washed twice with 120 g of acetone to obtain a white solid at room temperature (20-30 C). The white solid was dissolved in 1.3 kg of purified water and stirred.After 30 min, hydrochloric acid was added dropwise at room temperature to adjust the pH of the system to 1.5-2.0 to obtain a large amount of white solid. It was stirred for 1-2 hours, filtered, and the filter cake was washed twice with purified water. The resulting solid was dried to dryness at 50 ± 5 C to give a crude compound.Add 1 compound of crude product, 0.2 kg of absolute ethanol and 0 kg of purified water to a 1 L reaction flask, and warm to 75-80 C.Clear, heat for half an hour, cool to 0-5 C, filter, filter cake with a cold ethanol solution rinse, to obtain a white solid compound 1 boutique.The compound 1 was placed in a blast drying oven at a temperature of 55 C ± 5 C and dried for 5 h. Sampling, sampling every 2h 1Time, until the test (rapid moisture analyzer: 105 C, 10 min) loss on drying ? 0.5%, get Suwoleisheng intermediate products -Compound 1 was fine white crystalline solid 86 g, yield: 93%. Purity: 99.91%, Cu < 5 ppm. The synthetic route of 52548-14-8 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Yangzijiang Pharmaceutical Group Co., Ltd.; Zou Yiquan; Xu Jingren; Cai Wei; Xuan Jingan; Chen Lingwu; Ji Ye; Zhu Yunlong; Liu Jinfeng; Hu Tao; (8 pag.)CN109810067; (2019); A;,
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Related Products of 610-97-9,Some common heterocyclic compound, 610-97-9, name is Methyl 2-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 stirred slurry of methyl 2-iodo-benzoate (5.0 g, 0.019 mol) and N-bromosuccinimide (3.74 g, 0.021 mol) in acetic acid (10 mL) was added concentrated H2SO4 (10 mL) dropwise, keeping the temperature at 20-40 C. The mixture was stirred at room temperature for 88 hours and then heated at 50 C. for 4 hours. The mixture was cooled to 10 C., treated with 40 g of ice water, and extracted with 50 mL of CH2Cl2. The organic phase was washed in succession with 2×50 mL 5% NaHCO3, 50 mL 10% Na2S2O3, 50 mL water, and concentrated to colorless oil. The residue was purified by column chromatography (silica gel, 10:90 EtOAc:hexane) to provide the title compound. 1H NMR (CDCl3, 400 MHz) delta 7.92 (d, J=4 Hz, 1H), 7.83 (d, J=8 Hz, 1H), 7.27 (dd, J=8, 4 Hz, 1H), 3.92 (s, 3H); MS (DCl/NH3) [M+NH4]+ at 358, [M+NH3.NH4]+ at 375.

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-iodobenzoate, its application will become more common.

Reference:
Patent; Altenbach, Robert J.; Black, Lawrence A.; Chang, Sou-jen; Cowart, Marlon D.; Faghih, Ramin; Gfesser, Gregory A.; Ku, Yi-yin; Liu, Huaqing; Lukin, Kirill A.; Nersesian, Diana L.; Pu, Yu-ming; Curtis, Michael P.; US2005/256309; (2005); A1;,
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1450754-38-7, name is 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine, 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. Application In Synthesis of 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine

The steviol (30mg, 0.1mmol), K2CO3 (27mg, 0.2mmo 1) added to the dry flask, replace the nitrogen, then added 2mL anhydrous N, N-dimethylformamide (DMF), 3-(but-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine (1-1) (33mg0.13mmol) dissolved in 1mL N, N-dimethyl formamide, then added to the reaction under ice bath, and the mixture was heated to 70 C, and reacted for 6 hr. The mixture was subjected to thin layer chromatography (TLC), washed with 10% HCl, after washing with saturated brine and it was dried over anhydrous sodium sulfate and separation by column chromatography gave molecular probe 1 (white solid, 34 mg, 92% yield).

The synthetic route of 1450754-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Life Sciences Institute; Xiao Youli; Li Weichao; Zhou Yiqing; (27 pag.)CN108341781; (2018); A;,
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Reference of 5458-84-4, A common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, molecular formula is C7H6INO3, 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.

1-lodo-2-methoxy-4-nitro-benzene (6.01 g, 21.54 mmol) in absolute ethanol (127 mL) was cooled with an ice bath and treated with SnC (18.83 g, 99.31 mmol). The bath was removed and the mixture was stirred at room temperature for 4 h then poured into ice (300 mL), stirred and treated carefully with saturated aqueous sodium bicarbonate (250 mL) (pH 7-8). The solid was filtered with suction and the panel washed thoroughly with EtOAc (500 mL and 4 x 200 mL). The aqueous layer was separated, dried over sodium sulphate and evaporated. Purification of the crude by flash chromatography on silica gel (hexane/EtOAc 1/1) furnished the title compound (3.17 g, 59%).

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; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria, Gabriella; BERTRAND, Jay, Aaron; GNOCCHI, Paola; MOTTO, Ilaria; NESI, Marcella; PANZERI, Achille; VIANELLO, Paola; WO2013/14039; (2013); A1;,
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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. 54413-93-3, name is 2-Iodo-5-methoxybenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Iodo-5-methoxybenzoic acid

General procedure: A dry sealable vial was charged with sulfonimidamide 4a (368 mg, 2.00 mmol), 2-iodobenzoic acid (494 mg, 2.00 mmol), CuI (76 mg, 0.40 mmol), and K2CO3 (690 mg, 5.00 mmol) in anhyd DMF (5.0 mL). After heating to 100 °C for 2 h, the heterogeneous mixture was cooled to r.t. The mixture was diluted with water (10 mL), acidified with 2 M HCl and extracted with EtOAc (3 × 30 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by CombiFlash chromatography (silica gel, n-hexane/EtOAc, 6:4) to afford the desired product 7a as a cream solid; yield: 633 mg (90percent).

According to the analysis of related databases, 54413-93-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sen, Indira; Sasmal, Swarnendu; Hall, Roger G.; Pal, Sitaram; Synthesis; vol. 48; 21; (2016); p. 3743 – 3752;,
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Application of 401-81-0, 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. 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

To 1,4-dioxane (200 mL), 1,10-phenanthroline (2.52 g, 13.98 mmol) and copper(I) iodide (2.53 g, 13.28 mmol) were added, and cesium carbonate (36.16 g, 111.0 mmol), diethyl malonate (17.76 g, 111.0 mmol) and 3-iodobenzotrifluoride (25.12 g, 92.35 mmol) were then added thereto. After stirring under reflux for 7.5 hours, the reaction mixture was cooled to room temperature. To the reaction mixture, 1 N hydrochloric acid was added, and the mixture was filtered with a filter aid to remove solids. The filtrate was extracted twice with ethyl acetate, dried over magnesium sulfate, filtered, and the filtrate was distilled off under reduced pressure with an evaporator. The resulting crude product was purified by silica gel chromatography to obtain the title compound (21.26 g, 75.7%). 1H-NMR (CDCl3) delta 7.72-7.57 (3H, m), 7.49 (t, 1H, J=7.8 Hz), 4.66 (1H, s), 4.32-4.15 (4H, m), 1.32-1.22 (6H, m)

The chemical industry reduces the impact on the environment during synthesis 1-Iodo-3-(trifluoromethyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nippon Kayaku Kabushiki Kaisha; Hasegawa, Shinji; Kamo, Tomohiro; Kagohara, Yuma; Miyake, Takaaki; Kobayashi, Takeru; Matsuda, Ryusei; Asano, Shu; Kudamatsu, Akio; (43 pag.)US2018/310564; (2018); A1;,
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2468-56-6, name is 6-Iodohex-1-yne, 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. SDS of cas: 2468-56-6

To a stirred solution of iodo compound 20 (6.0 g, 28.84 mmol) in anhydrous DMF (30 mL) was added sodium azide (9.37 g, 144.20 mmol) at 0 C under argon atmosphere. The resulting mixture was stirred at rt for 3.5 h, then quenched with ice cold water (50 mL) and extracted with EtOAc (2 * 40 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentratedin vacuo. The crude residue was purified by silica gel column chromatography using 10% EtOAc/hexane to afford azide compound 21 (3.23 g, 91%) as a pale-yellow liquid. HRMS (ESI) m/z calcd for [C6H9N3+H]+: 124.0875, found 124.0218. 1H NMR (400 MHz, CDCl3): delta 3.31 (t, J = 6.7 Hz, 2H), 2.24 (td, J = 6.8, 2.5 Hz, 2H), 1.97 (t, J = 2.6 Hz, 1H), 1.77-1.70 (m, 2H), 1.65-1.58 (m, 2H). 13C NMR (100 MHz, CDCl3): 83.6, 68.9, 50.9, 27.8, 25.5, 18.0.

The synthetic route of 2468-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nagendra Reddy, Chintam; Grant, Gail E.; Ye, Qiuji; Powell, William S.; Patel, Pranav; Sivendran, Sashikala; Chourey, Shishir; Wang, Rui; Anumolu, Jaganmohan R.; Rokach, Joshua; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 116 – 125;,
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Adding a certain compound to certain chemical reactions, such as: 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, 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 31599-60-7, Product Details of 31599-60-7

To a solution of 1-iodo-2,3- dimethylbenzene (8) [prepared according to Chen, Y et al. Org. Lett. 2007, 9, 1899] (1 .93 g, 8.32 mmol) in carbon tetrachloride (40 mL) was added NBS (3.67 g, 20.62 mmol), AIBN (0.070 g, 0.43 mmol) and the resulting mixture was gently refluxed by irradiation with a halogen lamp (500 W) for 4 h. The precipitate was filtered and washed with a small amount of carbon tetrachloride. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc ( 1 00 ml), successively washed with 10% NaOH solution (20 mL), water (2 x 20 ml), 10% Na2S203 solution (20 mL), water (20 mL), brine (20 raL), and dried (Na2SC>4). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether) to give 1 .89 g (58.3%) of compound 9. NMR (CDC13) delta: 7.84 (dd, J=8.1 , 1 .1 Hz, 1 H), 7.33 (dd, J=7.6, 1 .1 Hz, l H), 6.97 (t, J=7.8 Hz, 1 H), 4.85 (s, 2H), 4.66 (s, 2H). The product contained ca. 15-20% of an inseparable impurity (supposedly l -bromo-2,3-bis(bromomethyl)benzene).A mixture of 1,2-bis(bromomethyl)-3-iodobenzene (9) (2.50 g, 6.41 mmol), diethyl 2-acetamidomalonate (1 .39 g, 6.41 mmol), and K2C03 (2.22 g, 1 6.06 mmol) in acetonitrile (40 mL) was refluxed for 70 h. The mixture was allowed to cool to ambient temperature, the precipitate was filtered and washed with a small amount of acetonitrile. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc (100 mL), washed successively with saturated NaHC03 solution (30 mL), water (2 x 30 mL), brine (30 mL), and dried (Na2S04). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 2 g of oil. The oil was dissolved in diethyl ether and kept in a refrigerator overnight. The precipitate was filtered and dried to give 0.4 g (14%) of a regioisomer diethyl 2-acetyl-5-iodo-l ,4-dihydroisoquinoline-3,3(2H)-dicarboxylate. NMR (CDC13) delta: 7.76 (d, J=8.0 Hz, 1H), 7.13 (d, J=7.5 Hz, 1 H), 6.94 (t, J = 7.7 Hz, 1H), 4.65 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 4.16 (q, J=7.1 Hz, 2H), 3.56 (s, 2H), 2.28 (s, 3H), 1 .22 (t, J=7.1 Hz, 3H), 1.22 (t, J=7.1 Hz, 3H). LCMS (ESI) m/z: 446 [M+H]+. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 0.95 g (33.2%) of compound (10).A solution of diethyl 2-acetyl-8-iodo-l,4-dihydroisoquinoline-3,3(2H)-dicarboxylate (10) (0.585 mmol) in 6 N HQ (10 mL) was refluxed for 5 h. The mixture was cooled and cone. NH4OH water solution was added until pH of the medium was ~7. The precipitate was filtered, washed with a small amount of water, and dried to give 0.305 g (76.7%) of compound (11). Because of a low solubility of the product in common deuterated organic solvents and deuterium oxide, the NMR spectrum was not informative. LCMS (ESI) m/z: 304 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid). LCMS (ESI) m/z: 256 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; JIRGENSONS, Aigars; LOZA, Einars; CHARLTON, Michael; FINN, Paul William; RIBAS DE POUPLANA, Lluis; SAINT-LEGER, Adelaide; (76 pag.)WO2016/129983; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 103440-52-4, 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. 103440-52-4 name is Methyl 2-Iodo-5-methylbenzoate, 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.

A degasssed mixture of ester EX-25A (10.35 g, 0.037 mol)), Pd(dba)3 (0.017 g, 0.018 mmol)), dppf (0.025 g, 0.045 mmol)) and Zn(CN)2 (2.6 g, 0.02 mol) in DMF (100 mL) was heated to 120 C. for 2 hours. The reaction mixture was poured into water and ethyl acetate. The organic layer was washed with water (2) and brine (1). The organic layer was collected, dried (MgSO4) and the solvent removed in vacuo to give 5.28 g methyl 2-cyano-5-methylbenzoate (EX-25B) as a brownish oil with m/z+1=176.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-Iodo-5-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Pharmacia Corporation; US6664255; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 20555-91-3, 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.

(R)-2-(3,4-Dichloro-phenylamino)-propionic acid (62% ee) A mixture of 6.00 g (22.00 mmol) 3,4-dichloroiodobenzene, 2.94 g (33.00 mmol) D-alanine, 0.42 g (2.20 mmol) copper(I) iodide, 0.96 g (4.40 mmol) 2-hydroxybenzaldehyde phenylhydrazone, 14.00 g (66.00 mmol) tri-potassium phosphate in 32 ml of N,N-dimethylformamide was stirred at 80 C. for 16 h under argon, then after cooling diluted with water and acidified to pH 3 by addition of 25% aq. HCl solution. The mixture was extracted with EtOAc (3*), the organic phases were washed with brine, dried (Na2SO4), filtered and evaporated. Flash chromatography (SiO2; dichloromethane/MeOH 95:5 to 4:1) afforded 3.11 g (60%) of the title compound (as 81:19 mixture of the (R) and (S) stereoisomers, BGB-175*0.25 column) as light brown solid. MS: 231.9 (M-H-, 2Cl).

The chemical industry reduces the impact on the environment during synthesis 1,2-Dichloro-4-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Green, Luke; Hartmann, Guido; Maerki, Hans P.; Mattei, Patrizio; US2011/92698; (2011); A1;,
Iodide – Wikipedia,
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