Month: November 2020

5471-81-8, A common compound: 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, 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.

(c) Preparation of methyl 3-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate Following the basic procedure of Example 7(f), by reacting 2.8 g (10 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid with 1.84 g (6.7 mmol) of methyl 3-methyl-4-iodobenzoate, 1.37 g (53%) of methyl 3-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate was obtained in the form of a yellow oil.

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-iodo-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; C.I.R.D. Galderma; US5723499; (1998); 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. 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., 19094-56-5

5-iodo-2-chlorobenzoic acid (33.895 g, 120 mmol) DCM (100 mL), DMF (0.175 g, 0.02 eq), Stir, Slowly add oxalyl chloride (12.3 ^, 1.2 called), After the drop is completed at room temperature reaction 21 , The solvent was removed by concentration under reduced pressure, Add DCM (lOOmL), Fluorobenzene (17.298 g, 1.5 eq) was added, AlCl3 (17.6 g, 1 leq) was added to the ice bath, After adding the reaction at room temperature for 3h, After TLC detection reaction was completed, Ice bath slowly add water (100mL), After stirring, The organic phase was washed with 10% NaCl (50 mL) The organic phase was concentrated under reduced pressure to give a pale yellow oil, Add isopropyl alcohol (lOOmL), add water (lOOmL), Ice bath 5CN 106928040 A manual 4/5 page stirring crystallization 2h, Filter, The filter cake was washed with isopropanol / water (1: 1) mixed solution (20 mL) Dried to give 42.1 g of an off-white solid of compound Vb, yield: 97.31%, purity: 99.17%.

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; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Ma Shuai; Zhou Weicheng; (7 pag.)CN106928040; (2017); A;,
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. 766-85-8, name is 3-iodoanisole, A new synthetic method of this compound is introduced below., 766-85-8

Step 10a. 1-Bromo-2-iodo-4-methoxybenzene (Compound 0104-13) Bromine (0.206 mL, 4.0 mmol) was added dropwise into a solution of compound 0103 (1.0 g, 3.20 mmol) in acetic acid (4.5 mL) with constant stirring overnight. Water (15 mL) was then added to the reaction mixture, and the product was extracted into hexane (3*7.5 mL). The combined organic layers were washed with 5% sodium sulfite (7.5 mL) and brine (7.5 mL), dried over magnesium sulfite, filtered and concentrated to leave an oily solid which was purified by chromatography on silica gel (petroleum) to yield the title product 0104-13 as a colorless oil (0.5 g, 37%): 1H NMR (CDCl3) delta 3.769 (s, 3H), 6.77 (dd, 1H, J1=3.0 Hz, J2=8.7 Hz), 7.39 (d, 1H, J=3.0 Hz), 7.47 (d, 1H, J=9.0 Hz).

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; Cai, Xiong; Qian, Changgeng; Zhai, Haixiao; US2008/234314; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

74-88-4, These common heterocyclic compound, 74-88-4, name is Iodomethane, 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.

UA-1 (100 mg, 0.22 mmol) was dissolved in DMF, then K2CO3(30.0mg,0.22mmol) and three drops of iodomethane were added at room temperature.The reaction end was monitored by TLC. After completion of reaction, the mixture was extracted with ethyl acetate and washed with saturated brine, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a white solid. The crude product was purified by column chromatography on silica gel with petroleumether-ethyl acetate (10:1) to obtain compound 2a, with a yield of 80.1%. m.p. 166.8-168.1C; ESI-MS: m/z 469.5[M+H]+.

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 74-88-4.

Reference:
Article; Meng, Yan-Qiu; Zhang, Liang-Feng; Liu, Dong-Ying; Liu, Li-Wei; Zhang, Yi; Zhao, Min-Jie; Journal of Asian Natural Products Research; vol. 18; 3; (2016); p. 280 – 288;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1878-94-0, name is 2-(4-Iodophenoxy)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. 1878-94-0

Step 3: N-(3-Fluoro-4-methanesulfonylamino-benzyl)-2-(4-iodo- phenoxy)-acetamide; 3-Fluoro-4-methanesulfonylamino-benzylamine HCI salt (120 mg, 0.471 mmol), NMP (0.25 ml), and (4-iodo-phenoxy)-acetic acid (121 mg, 0.435 mmol) were added in THF (50 ml). After the mixture was stirred for 10 min, DMTMM (138 mg, 0.500 mmol) was added into the mixture. The reaction mixture was stirred overnight. The reaction solvent was removed in vacuo. The resulting residue was extracted with ethyl acetate (60 ml) and H2O (30 ml). The organic layer was washed with saturated K2CO3 (30 ml), 5% HCI solution (30 ml) and brine (30 ml). The organic layer was dried with MgSO4 and concentrated in vacuo. The residue was purified with column chromatography to yield the title compound (172 mg, 83%) as a white solid.Mp: 172 – 153 0C; 1H NMR (300 MHz, CDCI3): delta 7.60 (d, 2H), 7.53 (m, 1H), 7.08 (d, 2H), 6.89 (br, 1H), 6.69 (m, 1 H), 6.45 (br, 1 H), 4.52 (m, 2H), 4.50 (s, 2H), 3.02 (s, 3H)IR (neat, cm’1): 1674, 1650, 1523, 1482, 1330, 1152. MS : 478 (M)

Statistics shows that 1878-94-0 is playing an increasingly important role. we look forward to future research findings about 2-(4-Iodophenoxy)acetic acid.

Reference:
Patent; AMOREPACIFIC CORPORATION; WO2007/120012; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

696-41-3, Name is 3-Iodobenzaldehyde, 696-41-3, 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.

General procedure: A 25-mL flask was charged with Pd(OAc)2 (1.2 mg, 0.005 mmol), 1-iodo-4-nitrobenzene (1a, 127.0 mg, 0.5 mmol), K2CO3 (141.0 mg, 1.0 mmol), H2O (0.5 mL), and PEG 400 (2.0 mL); the flask was subjected to standard cycles (3 ¡Á) of evacuation and back-filling with dry and pure CO. The mixture was stirred at r.t. for the indicated time. The mixture was poured into sat. aq NaCl (15 mL), acidified to pH 3 with 3 M aq HCl, and extracted with EtOAc (3 ¡Á 15 mL). The solvent was removed from the combined organic phases on a rotary evaporator. The crude product was purified by column chromatography (silica gel, PE-EtOAc-HCO2H, 25:1:1) to afford 2a as a light yellow solid; yield: 75mg (90%); mp 238.0-239.3 C. 1H NMR (400 MHz, DMSO-d6): delta = 13.68 (br s, 1 H), 8.30 (d, J = 8.0 Hz,2 H), 8.14 (d, J = 8.0 Hz, 2 H). 13C NMR (100 MHz, DMSO-d6): delta = 165.9, 150.0, 136.4, 130.7, 123.8.

Statistics shows that 3-Iodobenzaldehyde is playing an increasingly important role. we look forward to future research findings about 696-41-3.

Reference:
Article; Han, Wei; Jin, Fengli; Zhou, Qing; Synthesis; vol. 47; 13; (2015); p. 1861 – 1868;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9, 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. 624-75-9, name is 2-Iodoacetonitrile, A new synthetic method of this compound is introduced below.

As shown in step 5-ii of Scheme 5, 5-bromo-2-(lH-pyrazol-4-yl)isoindolin-l-one (1.2 g, 4.32 mmol) was combined with cesium carbonate (1.69 g, 5.18 mmol) in DMF (10 mL) in a sealable tube and nitrogen gas was bubbled through the solution for 5 minutes. 2- Iodoacetonitrile (1.08 g, 468 mu, 6.47 mmol) was added and the tube was sealed and heated to 110 C in an oil bath for 18 hours. Additional iodoacetonitrile added (0.5 mL) and the reaction mixture was heated for an additional 24 hours. The reaction mixture was poured into H20/EtOAc and the resulting dark brown solid was collected by filtration. The solid was washed with MeOH and then diethyl ether to provide 2-[4-(5-bromo-l-oxo-isoindolin-2- yl)pyrazol-l-yl]acetonitrile (Compound 2020, 920 mg, 2.9 mmol, 67% yield): ESMS (M+H) 319.04; 1H NMR (DMSO-d6) delta 8.35 (s, 1H), 7.92 (m, 2H), 7.70 (m, 2H), 5.53 (s, 2H), 4.88 (s, 2H).

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; VERTEX PHARMACEUTICALS INCORPORATED; ARONOV, Alex; COME, Jon, H.; DAVIES, Robert, J.; PIERCE, Albert, C.; WANG, Jian; NANTHAKUMAR, Suganthini; CAO, Jingrong; BANDARAGE, Upul, K.; KRUEGER, Elaine; TIRAN, Amaud, Le; LIAO, Yusheng; MESSERSMITH, David; COLLIER, Philip, N.; GREY, Ronald; O’DOWD, Hardwin; HENDERSON, James, A.; GRILLOT, Anne-Laure; WO2011/87776; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

52548-14-8, 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. 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-iodo-5-methylbenzoic acid (2a; 0.2 mmol, 1equiv), styrene 1a (0.8 mmol, 4 equiv) and NaHCO3 (0.26 mmol,1.3 equiv) in DMSO (4 mL) was put into a quartz reaction tube(10 mL). N2 was flowed in for 10 min, then the tube was sealedand exposed to illumination with a high-pressure mercurylamp at 300 nm wavelength for 6 h. Water (20 mL) was added tothe reaction system and the mixture was extracted with ethyl acetate (3 ¡Á 20 mL). The organic phase was washed with saturatedsalt water, dried with anhydrous sodium sulfate, and thecrude products were obtained under reduced pressure and concentration.The purified products were purified by silica gelcolumn chromatography (PE/EtOAc, 10:1), and the product 7-methyl-3-phenylisochroman-1-one 3a (75%) was obtained as apale-yellow liquid. 1H NMR (400 MHz, CDCl3): delta = 7.97 (s, 1 H), 7.52-7.33 (m, 6 H), 7.17 (d, J = 7.7 Hz, 1 H), 5.53 (dd, J = 12.0,3.2 Hz, 1 H), 3.29 (dd, J = 16.3, 12.0 Hz, 1 H), 3.10 (dd, J = 16.4,3.2 Hz, 1 H), 2.41 (s, 3 H). 13C NMR (151 MHz, CDCl3): delta = 165.6,138.6, 137.7, 135.0, 134.8, 130.6, 128.6, 128.6, 127.2, 126.1,124.8, 80.0, 35.2, 21.0. HRMS (ESI): m/z [M + H]+ calcd for C16H15O2: 239.1067; found: 239.1066.

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; Zhang, Xiao; Huang, Binbin; Yang, Chao; Xia, Wujiong; Synlett; vol. 29; 1; (2018); p. 131 – 135;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 63262-06-6 name is 1,4-Dibromo-2,5-diiodobenzene, 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. 63262-06-6

9.75 g of compound 3 and 0.562 gBis(triphenylphosphine)palladium dichlorideAnd 2-tributylstannylthiophene was dissolved in 70 mL of toluene.Stirring at 80 C for 2 days,It was then cooled to room temperature.Remove all liquids by rotary evaporator.The residue was recrystallized from methanol to give 5.6 g of Compound 4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Dibromo-2,5-diiodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Ningbo Materials Technology And Engineering Institute; Ge Ziyi; Xie Lingchao; Xiao Jingbo; Huang Jiaming; Peng Ruixiang; (23 pag.)CN109970761; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 25252-00-0 name is 2-Bromo-5-iodobenzoic acid, 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. 25252-00-0

To a solution of 2-bromo-5- iodobenzoic acid (11.4 g, 34.8 mmol) in dichloromethane (140 mL) was added methanol (17 mL) followed by trimethylsilyldiazomethane solution (2M in hexanes, 19.2 mL, 38.4 mmol). The reaction was stirred at room temperature for twelve hours, quenched by the dropwise addition of acetic acid (5 mL) and thoroughly concentrated. The resulting residue was dissolved in tetrahydrofuran. To this solution was added diisobutylaluminum hydride solution (1M in DCM, 50 mL, 50 mmol) and the reaction was stirred at room temperature. After sixteen hours, more diisobutylaluminum hydride solution (1M in DCM, 50 mL, 50 mmol) was added. After 96 more hours at room temperature the reaction was diluted with ether (100 mL) and quenched by the sequential addition of water (4 mL), 15% aqueous NaOH solution (4 mL) and water (10 mL). After thirty minutes the mixture was filtered through Celite and the filtrate was concentrated. The resulting residue was dissolved in dimethylformamide (75 mL). To this solution was added imidazole (6.1 g, 89.6 mmol) and r-butyldimethylchlorosilane (6.8 g, 45.1 mmol). The reaction was stirred at room temperature for two hours and then diluted with ethyl acetate. The organics were washed with saturated aqueous NH4CI solution, water and brine. The organic layer was dried (MgS04) and concentrated, and the resulting residue was purified by flash column chromatography to yield (2-bromo-5-iodobenzyloxy)-(tert-butyl)dimethylsilane (9.2 g, 62%).

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

Reference:
Patent; GILEAD SCIENCES, INC.; BACON, Elizabeth, M.; COTTELL, Jeromy, J.; KATANA, Ashley, Anne; KATO, Darryl; KRYGOWSKI, Evan, S.; LINK, John, O.; TAYLOR, James; TRAN, Chinh, Viet; TREJO MARTIN, Teresa, Alejandra; YANG, Zheng-Yu; ZIPFEL, Sheila; WO2012/68234; (2012); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com