Tag: M.W=100-200

The chemical industry reduces the impact on the environment during synthesis 627-32-7, name is 3-Iodo-1-propanol, I believe this compound will play a more active role in future production and life. 627-32-7

Example 31 Synthesis of OS-1-CA Conjugate 48 (FIG. 24) Compound 46 To a solution of oseltamivir carboxylic acid N-Boc derivative (64, 60 mg, 0.16 mmol) in MeOH (0.5 mL) was added KOH (6.87 mg, 0.17 mmol). The mixture was stirred at room temperature for 30 min, and then concentrated under reduced pressure. The residue was dissolved in DMF (0.5 mL), and then added 3-iodo-1-propanol (17 mL, 0.19 mmol). After stirring at 50 C. for 4 h, the mixture was evaporated under reduced pressure. The residues was dissolved in CH2Cl2 (10 mL) and extracted with 1 M HCl and brine, dried over MgSO4, concentrated under reduced pressure, and purified by flash silica gel column chromatography (EtOAc/hexane, 2:1) to afford compound 65 (50 mg, 72%). C22H38N2O7; white solid; mp 93-95 C.; TLC (EtOAc/n-hexane, 2:1) Rf=0.31; [alpha]D22=-81.9 (c=1.0, CH2Cl2); IR (film) 3309, 2964, 2935, 2878, 1686, 1536, 1458, 1392, 1368, 1295, 1255, 1172, 1057 cm; 1H NMR (400 MHz, CDCl3) delta 6.77 (1H, s), 5.88 (1H, d, J=8.8 Hz), 5.11 (1H, d, J=9.6 Hz), 4.28-4.31 (2H, m), 4.01-4.08 (1H, m), 3.95 (1H, d, J=7.2 Hz), 3.73-3.82 (1H, m), 3.70 (2H, t, J=6.0 Hz), 3.30-3.34 (1H, m), 2.72 (1H, dd, J=17.6, 5.2 Hz), 2.26 (1H, dd, J=18.0, 10.0 Hz), 1.97 (3H, s), 1.87-1.93 (2H, m), 1.47-1.57 (4H, m), 1.41 (9H, s), 0.85-0.91 (6H, m); 13C NMR (100 MHz, CDCl3) delta 170.9, 165.9, 156.2, 138.1, 128.8, 82.3, 79.5, 75.8, 61.8, 58.6, 54.6, 49.3, 31.5, 30.9, 28.4 (3*), 26.2, 25.7, 23.3, 9.7, 9.3; HRMS calcd for C22H39N2O7: 443.2757, found: m/z 443.2753 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 627-32-7. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Academia Sinica; Wong, Chi-Huey; Fang, Jim-Min; Liu, Kung-Cheng; Jan, Jia-Tsrong; Cheng, Yih-Shyun E.; Cheng, Ting-Jen R.; US2013/274229; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common compound: 624-75-9, name is 2-Iodoacetonitrile, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 624-75-9

j181j To a mixture of 5-bromo-2-isopropyl-4-methoxy-phenol from step 4 (0.831 g, 3.4 mmol) and K2C03 (0.562 g, 4.1 mmol) in 17 mL dimethyl formamide (DMF) was added iodoacetonitrile (0.594 g, 3.6 mmol). The mixture was warmed to 60 C for 30 minutes and then allowed to cool to room temperature. After cooling to room temperature the mixture was taken up in 50 mL of H20 and extracted with 1:1 toluene/ethyl acetate, washed with H20 and then with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a crude solid. Purification via flash chromatography (1:1 hexane/CH2C12) afforded (5-bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (0.611 g, 63%) as a while 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, 624-75-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AFFERENT PHARMACEUTICALS, INC.; FORD, Anthony P.; PATON, Julian; (86 pag.)WO2016/4358; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

74-88-4, 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. 74-88-4, name is Iodomethane, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of compound2and K2CO3in DMF was added methyl iodide,bromoethaneorbromopentaneand, the resulting mixture was stirred with heating at room temperature for 6h. The mixture was extracted with ethyl acetate, then combined the organicphases,dried(MgSO4) and concentrated under pressure to give the crude product. The crude product was purified by the silica gel column chromatography (petroleum ether /ethyl acetate, 5:1) to give the desired product4a-c.

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:
Article; Wu, Jie; Zhang, Zhi-Hong; Zhang, Lin-Hao; Jin, Xue-Jun; Ma, Juan; Piao, Hu-Ri; Bioorganic and Medicinal Chemistry Letters; vol. 29; 6; (2019); p. 853 – 858;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

144-48-9, 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. 144-48-9 name is 2-Iodoacetamide, 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.

Sodium hydride (0.57 g of a 60% dispersion in mineral oil, 0.014 mol) was added in portions at 23 C to a stirred solution of the alcohol (4) (4.22 g, 0.012 mol) in dry dimethyl formamide (60 mL). After 10 min a solution of iodoacetamide (2. 68 g, 0.014 mol) in dimethyl formamide (10 mL) was added and the solution was stirred at 23 C for 16 h. Silica gel was added and the reaction mixture was adsorbed directly onto it by concentration of the mixture to dryness in vacuo. The product was chromatographed on silica. Elution with ethyl acetate gave isomer (6) as a white solid (3.16 g, 63%). Elution with methanol/ethyl acetate (5: 95) gave the required product (5) as a foamy solid (4.92 g-contains sodium iodide as well). This material was used directly in the next step. APCI-MS Found [M+H] =416,414.

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

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/89763; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9, The chemical industry reduces the impact on the environment during synthesis 624-75-9, name is 2-Iodoacetonitrile, I believe this compound will play a more active role in future production and life.

General procedure: Individual solutions of secondary N-alpha-trimethylsilylmethyl-N-benzylamines19 (5mmol) in acetonitrile (100mL) containing K2CO3 (10mmol) and 2-iodoacetonitrile (4.5mmol) were stirred for 12hat room temperature and concentrated in vacuo to give residues that were partitioned between water and CH2Cl2. The CH2Cl2 layers were dried and concentrated in vacuo to afford residues that were subjected to silica gel column chromatography (EtOAc/hexane=1: 15 – 1: 30) to yield corresponding alpha-aminonitiriles 11a18 (91%), 11b (74%), 11c (78%), 11d (85%), 11e (75%), 11f (75%), 11g (74%), 11h (75%), 11i (78%), 11j (78%) and 11k (66%).

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

Reference:
Article; Lim, Suk Hyun; Cho, Dae Won; Choi, Jungkweon; An, Hyunjun; Shim, Jun Ho; Mariano, Patrick S.; Tetrahedron; vol. 73; 44; (2017); p. 6249 – 6261;,
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. 624-76-0, name is 2-Iodoethanol, This compound has unique chemical properties. The synthetic route is as follows., 624-76-0

A solution of 2,3,3-trimethyl-3H-indole (1 ml, 6.3 mmol) and 2-iodoethanol (0.56 ml, 8.8 mmol) in MeCN (4 mL) was refluxed for 1 day. After being cooled to r.t., the reaction mixture was suspended in hexane, and the precipitated solid was sonicated and filtered. A part of the obtained purple solid (53 mg out of 1.37 g) was dissolved in 1N KOH (2 mL) and stirred at r.t. for 30 min. After extraction with ether, the organic layer was evaporated to afford 4 as yellow oil, which was used for the next reaction without further purification. A solution of 5-nitrososalicylaldehyde (38 mg, 0.23 mmol) and the obtained 4 in EtOH (5 mL) was refluxed for 4 hours. The mixture was evaporated and purified by column chromatography (silica gel; eluent, hexane_AcOEt=1:1) to afford purple crystal 5 (56 mg, 66% based on 2,3,3-trimethyl-3H-indole). MS(EI): 352(M+, 15), 337(5), 321(9), 83(100); HRMS(EI): M+352.1411 (calc.352.1423); 1H NMR(CDCl3) delta1.20 (s, 3H), 1.30 (s, 3H), 3.34 (ddd, J=5.1, 5.1, 14.7 Hz, 1H), 3.47 (ddd, J=5.5, 7.3, 14.7 Hz, 1H), 3.69-3.82 (m, 2H), 5.89 (d, J=10.5 Hz, 1H), 6.67 (d, J=7.5 Hz, 1H), 6.77 (d, J=8.5 Hz, 1H), 6.90 (dd, J=7.5, 7.5 Hz, 1H), 6.91 (d, J=10.5 Hz, 1H), 7.10 (dd, J=1.1, 7.5 Hz, 1H), 7.50 (ddd, J=1.1, 7.5, 7.5 Hz, 1H), 8.00 (d, J=2.5, 1H), 8.03 (dd, J=2.5, 8.5 Hz, 1H).

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; WISCONSIN ALUMNI RESEARCH FOUNDATION; US2007/195309; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, 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. 624-75-9

The compound obtained in Example 21 (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 by heating. 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 to the residue were added 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 [4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile and [4-(2-chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile as yellow oil. These two regioisomers (4.78 g, 92%) were used in the next reaction step without separation.[4-(2-Chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.29 (s, 3H), 3.71 (s, 3H), 5.19 (s, 2H), 6.73 (s, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.06 (d, J=4.4 Hz, 1H), 7.26 (s, 1H), 7.79 (s, 1H), 8.24 (d, J=4.8 Hz, 1H); 13C NMR (CDCl3) delta 21.53, 39.97, 55.29, 110.91, 111.12, 113.65, 115.67, 118.75, 121.59, 121.65, 122.78, 130.58, 132.37, 140.16, 143.28, 149.68, 151.45, 151.79, 159.71, 162.33.[4-(2-Chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.83 (s, 3H), 4.94 (s, 2H), 6.63 (s, 1H), 6.74 (s, 1H), 6.92-6.96 (m, 2H), 7.19 (s, 1H), 7.93 (s, 1H), 8.17 (d, J=5.2 Hz, 1H); 13C NMR (CDCl3) delta 21.56, 37.78, 55.48, 112.15, 113.91, 117.08, 118.16, 119.88, 121.36, 122.48, 128.46, 139.57, 141.60, 142.19, 142.85, 149.78, 151.95, 160.48.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 22 (300 mg, 0.89 mmol), 3-pyridineboronic acid (0.13 g, 1.06 mmol), dichlorobis(triphenylphosphine)palladium (II) (31 mg, 0.04 mmol) and potassium carbonate (130 mg, 0.89 mmol), and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled at room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL¡Á3). 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, 2:1, v/v): (62 mg, 55%); m.p. 81-82 C.; 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.80 (s, 3H), 4.95 (s, 2H), 6.73 (s, 1H), 6.80 (s, 1H), 6.94 (s, 1H), 7.11 (d, J=5.0 Hz, 1H), 7.34 (dd, J=3.0, 4.8 Hz, 1H), 7.54 (s, 1H), 8.00 (s, 1H), 8.15 (d, J=7.8 Hz, 1H), 8.54 (d, J=5.1 Hz, 1H), 8.60 (d, J=4.4 Hz, 1H), 8.89 (s, 1H); 13C NMR (CDCl3) delta 21.62, 37.79, 55.50, 112.38, 114.08, 116.81, 118.15, 119.21, 120.35, 122.59, 123.59, 128.90, 134.30, 134.78, 139.57, 140.71, 141.57, 141.97, 148.02, 149.92, 150.34, 154.99, 160.48.

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 624-75-9.

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

624-76-0, The chemical industry reduces the impact on the environment during synthesis 624-76-0, name is 2-Iodoethanol, I believe this compound will play a more active role in future production and life.

Compound 5 (1.41 g, 0.0043 mol) and potassium carbonate (1.78 g, 0.0129 mol) were added into a round bottom flask. The flask was made free of water and oxygen. The mixture was dissolved with DMF (60 ml). Then 2-iodo-ethanol (0.67 ml, 0.0086 mol) was slowly added dropwise. The reaction was raised to 50 C. and stirred. After completion of the reaction, the reaction was dissolved with ethyl acetate (250 ml), and then extracted with water (3¡Á60 ml) to remove DMF, and washed with saturated brine, dried with anhydrous magnesium sulfate, filtered, evaporated to dryness, and dried by pumping to provide a white solid 6 (1.475 g, 93.35%).

The chemical industry reduces the impact on the environment during synthesis 624-76-0. I believe this compound will play a more active role in future production and life.

Reference:
Patent; YANTAI UNIVERSITY; WANG, Hongbo; HONG, Xuechuan; ZHU, Xi; WANG, Pengyu; LV, Guangyao; FU, Jie; LUO, Huairong; ZHANG, Jianqiao; WEN, Meng; QU, Chunrong; ZHU, Jinmei; HU, Xianming; (7 pag.)US2016/102066; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 624-76-0, name is 2-Iodoethanol, 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. 624-76-0

General procedure: To a stirred solution of compound 42 (1.0 eq) and the corresponding alkyl iodide (1.0 eq) in THF (0.1 M) was added Et3N (2.0 eq) and themixture was stirred at room temperature for 20 h. The reaction mixture was purified by preparative HPLC (direct injection of reaction mixture) and the combined HPLC fractions were concentrated. The residue was dissolved in DCM and then washed with 2M aqueous NaOH, brine, dried over anhydrous Na2SO4 and then concentrated to give the product.

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 624-76-0.

Reference:
Article; Arns, Steve; Balgi, Aruna D.; Shimizu, Yoko; Pfeifer, Tom A.; Kumar, Nag; Shidmoossavee, Fahimeh S.; Sun, Sharon; Tai, Sheldon S.-H.; Agafitei, Olga; Jaquith, James B.; Bourque, Elyse; Niikura, Masahiro; Roberge, Michel; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 64 – 73;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-76-0, name is 2-Iodoethanol, 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. 624-76-0

Preparation of tert-butyl(2-iodoethoxy)dimethylsilane After 2-iodoethanol (1.72 g, 10 mmol) was dissolved in dimethylformamide (8 mL), imidazole (0.817 g, 12 mmol) and tert-butyldimethylsilyl chloride (1.66 g, 11 mmol) were added thereto, and the mixture was stirred for 4 hours at 30 C. to 40 C. Water (50 mL) was added to the reaction solution, and the result was extracted with an ethyl acetate/normal-hexane=1/1 solution (100 mL). The organic layer was washed again with salt water (30 mL*3), dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 2.85 g (90%) of a target compound. This compound was used as it was for the next reaction without purification.

Statistics shows that 624-76-0 is playing an increasingly important role. we look forward to future research findings about 2-Iodoethanol.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; SON, Jong Chan; KIM, Bong Jin; KIM, Jae Hak; LEE, Ill Young; YUN, Chang Soo; LEE, Sang Ho; LEE, Chong Kgo; US2014/249162; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com