Tag: M.W=300-400

Application of 188815-32-9,Some common heterocyclic compound, 188815-32-9, name is 3-Bromo-5-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

50.0 g (152.9 mmol) of 3-bromo-5-iodobenzoic acid was added to a 1.0 L flask and dissolved in 70 mL of chloroform under a nitrogen atmosphere.88.7 mL (1.22 mol) of thionyl chloride (SOCl2) was added, and the mixture was stirred under reflux for 18 hours. After the temperature was lowered to room temperature, the reaction solution was concentrated under reduced pressure to obtain 52.0 g (yield: 98.4%) of a yellow solid compound (Intermediate (6))

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

Reference:
Patent; WS Co.,Ltd.; Kim, Yoo Li; Koo, Cha Ryong; Oh, Yoo Jin; (30 pag.)KR101652323; (2016); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 31827-94-8, 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. 31827-94-8, name is 2-Bromo-1-(4-iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows.

Into a 25 mL eggplant-shaped flask was added 1 mmol of N-(4-trifluoromethylphenyl)thiourea.1.05 mmol alpha-bromo-4-iodophenone,Add 10mL of ethanol to dissolve, add 1.5mmoL of triethylamine,Reflux reaction. After TLC tracks the reaction,The temperature of the reaction solution was lowered to room temperature, and the solvent was distilled off under reduced pressure.Column chromatography of the residue (eluent: petroleum ether-ethyl acetate) yields the target compound,White solid, yield 82%.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-(4-iodophenyl)ethanone. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shanghai Pharmaceutical Industry Institute; East China University of Science and Technology; Chen Daijie; Xu Xiaoyong; Shao Lei; Li Zhong; Dong Xiaojing; Hou Shuang; Zhang Junliang; Wang Rong; (81 pag.)CN107629022; (2018); 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. 450412-28-9, name is 1-Bromo-3-chloro-2-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H3BrClI

A 500-mL round-bottom flask under N2 atmosphere was charged sequentially with Pd(Ph3P)4, l-bromo-3-fluoro-2-iodobenzene (10 g, 0.032 mol) in toluene (80 mL), 2N aqueous sodium carbonate (55 mL) and 3-methylphenylboronic acid (5.16 g, 0.032mol) dissolved in ethanol (40 mL). This mixture was heated at reflux under N2 for 12 h and cooled to rt. The mixture was partitioned between water and EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography to give 6-bromo-2-chloro-3′-methyl-biphenyl (6 g, 67%). 1H NMR (400MHz, CD3OD): 6.90-7.00 (t, 2H), 7.14-7.24 (m, 2H), 7.26-7.33 (t, IH), 7.44-7.50 (d, IH), 7.58-7.62 (d, IH); MS (E/Z): 281 (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 450412-28-9.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; WO2007/117560; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 450412-29-0, A common heterocyclic compound, 450412-29-0, name is 1-Bromo-3-fluoro-2-iodobenzene, molecular formula is C6H3BrFI, 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.

200 g(664 mmol) 1-bromo-3-fluoro-2-iodobenzene, 101 g (664 mmol) of 2-methoxy-phenylboronicacid and sodium tetraborate 137.5 g (997 mmol) were dissolved in 1000 ml THFand 600 ml water, and degassed. 9.3 g (13.3 mmol) of bis (triphenylphosphine)palladium (II) chloride and 1 g (20 mmol) hydrazinium hydroxide was added. The reaction mixture was stirred at 70C for 48 h under a protective gas atmosphere, cooled, washed several times with water, dried and evaporated. The reaction mixture was purified by silica gel column chromatography using toluene/heptane (2:1). Yield 155 g (553 mmol), 83%.

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; Merck Patent GMBH; Faram, Amir Hossain; Yatsi, Anya; Evemilley, Thomas; Grossman, Tobias; Krevor, Jonas Valentine; Tobelmann, Laruese; (100 pag.)KR2016/28524; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

148870-57-9, name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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. category: iodides-buliding-blocks

A mixture of (8)-N- [(4,5-dimethoxybenzocyclobut- 1 -yl)methyl] -N-(methyl)amine hydrochloride (50.36g) and dimethyl formamide (200mL) ws stirred for about 5mm andpotassium carbonate (178.46g) was added to it. The reaction mixture was stirred for about lh at about room temperature. The reaction mixture was cooled to about 5C to about 10C. 7,8-dimethoxy-3 -[3-iodopropyl]- 1,3 -dihydro-2H-3 -benzazepin-2-one (I 00g) prepared as in Example 8, was added to the stirred reaction mixture. The reaction mixture was stirred for about 6h at about 20C to about 25C. The reaction mixture was quenchedinto chilled demineralized water at about 5C to about 10C. The reaction mixture was acidified to pH of about I to about 2 using concentrated hydrochloric acid and ethyl acetate was added to it. The reaction mixture was stirred and the two layers were separated. The aqueous layer was basified to pH of about 8 to about 9.5 using 20-25% aqueous ammonia solution and ethyl acetate was added to it. The reaction mixture wasstirred and the two layers were separated. The organic layer was treated with activated charcoal, stirred at about room temperature for about 30mm, filtered over hyflo bed and washed with ethyl acetate.To the above ethyl acetate layer, was added 10% palladium charcoal (15g) and the reaction mixture was hydrogenated in an autoclave under hydrogen pressure of about8kg/cm3 to about IOkg/cm?at about 65C to about 70C for about 6h. After completion of reaction, the reaction mixture is cooled to about 20C to about 25Cand filtered overhyflo bed. The hyflo bed was washed with ethyl acetate. The reaction mixture was concentrated at about below 50C under reduced pressure and acetonitrile (400mL) and isopropyl alcohol hydrogen chloride (IPA-HCI) (3OmL) was added to it at about 5C toabout 10C. The reaction mixture was stirred at about 10C to about 15C for about 3h. The reaction mixture was concentrated at about below 50C under reduced pressure and acetonitrile (400mL) was added to it. The reaction mixture was heated to about 80C to about 85C and stirred at about the same temperature for about lh. The reaction mixture was cooled and the solid obtained was filtered, washed with acetonitrile and dried at about 50C to about 55C.Yield: 85%; 1-IPLC purity: > 98%

The synthetic route of 148870-57-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS LIMITED; GLENMARK GENERICS LIMITED; BHIRUD, Shekhar Bhaskar; BHUSHAN, Kumar Hari; ZOPE, Sunil Sudhakar; PATIL, Dipak Vinayak; DHEBADE, Pramod Amrutrao; CHAND, Prem; WO2014/102827; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 51839-15-7, These common heterocyclic compound, 51839-15-7, name is Dimethyl 5-iodoisophthalate, 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.

Intermediate LXII: Dimethyl-5-trifluoromethyl isophthalate; To a solution of dimethyl 5-iodoisophthalate (1 g, 3.12 mmol) in 1:1 DMF/HMPA was added Methyl- 2,2-difluoro-2( fluorosulfonyl) acetate (3 g, 15.6 mmol) and Copper (I) Iodide (2.9 mg, 15.6 mmol) and the reaction mixture heated to. 80 C for 16 h. The reaction was cooled to rt and diluted with ethyl acetate (200 mL) The solvent was decanted and the copper salts washed with an additional 100 mL of ethyl acetate. The organics were poured into water (200 mL ) the phases separated and the aqueous extracted with Ethyl acetate ( 100mL) dried over anhydrous sodium sulfate, filtered and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with dichloromethane. to give dimethyl-5-trifluoromethyl isophthalate. : :?H NMR (400 MHz, CDC13) No. 8.85 (s, 1H), 8.48 (s, 2H), 4.01 (s, 6H). LCMS [(M) +H]+ = 263.

The synthetic route of 51839-15-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2005/103020; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 791642-68-7, name is 4-Bromo-1-iodo-2-methoxybenzene, 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 791642-68-7, Product Details of 791642-68-7

Step 2: 4-bromo-1-iodo-2-methoxybenzene (647 mg, 2.07 mmol), tert-butyl piperazine-1-carboxylate (350 mg, 1.88 mmol), sodium tert-butoxide (541 mg, 5.6 mmol), Pd2(dba)3 (52 mg, 0.056 mmol) and XantPhos (98 mg, 0.17 mmol) were taken up in toluene (18 mL) under Ar. The reaction mixture was stirred for 18 h and was then heated to 45 C. After an additional 2.5 h, the temperature was increased to 65 C. After an additional 3 h, the reaction mixture was cooled and partitioned between water and EtOAc. The phases were separated, and the organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (0-25% EtOAc in hexanes) to afford tert-butyl 4-(4-bromo-2-methoxyphenyl)piperazine-1-carboxylate 7.09.

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, 4-Bromo-1-iodo-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 1258298-01-9, 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. 1258298-01-9 name is 2,6-Dichloro-4-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.

General procedure: A mixture of 2-chloropyridine-3,4-diamine(2.80 g, 19.4mmol), 2,6-dichlorobenzoic acid(3.71 g, 19.4mmol)andpolyphosphoricacid (50 g) was heated at 190 Cfor 3 h with stirring. The mixture was cooled to room temperature and poured into ice/water. The resulting mixture was neutralized by addition of aq. saturated Na2CO3solution. The crude product was collected by filtration, washed with water, and dried to afford a brown solid(5.4 g, 97% yield).1H NMR(DMSO-d6, 500 MHz):delta13.08 (s, 1H), 11.21 (s, 1H), 7.67-7.58 (m, 3H),7.15 (m, 1H), 6.49 (d,J= 7.0 Hz, 1H).LCMS(ESI) m/z: 280.0 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichloro-4-iodobenzoic acid, and friends who are interested can also refer to it.

Reference:
Article; Liang, Jun; Van Abbema, Anne; Balazs, Mercedesz; Barrett, Kathy; Berezhkovsky, Leo; Blair, Wade S.; Chang, Christine; Delarosa, Donnie; DeVoss, Jason; Driscoll, Jim; Eigenbrot, Charles; Goodacre, Simon; Ghilardi, Nico; MacLeod, Calum; Johnson, Adam; Bir Kohli, Pawan; Lai, Yingjie; Lin, Zhonghua; Mantik, Priscilla; Menghrajani, Kapil; Nguyen, Hieu; Peng, Ivan; Sambrone, Amy; Shia, Steven; Smith, Jan; Sohn, Sue; Tsui, Vickie; Ultsch, Mark; Williams, Karen; Wu, Lawren C.; Yang, Wenqian; Zhang, Birong; Magnuson, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4370 – 4376;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 16355-92-3,Some common heterocyclic compound, 16355-92-3, name is 1,10-Diiododecane, molecular formula is C10H20I2, 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.

2,2′-(4S,4’S)-8,8′-(decane-1,10-diylbis(oxy)bis(6-(4-chlorophenyl)-1-methyl- 4H-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine-8,4-diyl))bis(N-ethylacetamide) [Example 11]: A suspension of 2-(4S)-6-(4-chlorophenyl)-8-hydroxy-1-methyl-4H- benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepin-4-yl)-N-ethylacetamide (208 mg, 0.507 mmol) in acetonitrile (10 mL) was charged with K2CO3 (82 mg, 0.6 mmol) and 1,10-diiododecane (100 mg, 0.254 mmol) and the resulting mixture was heated at 80 oC for 12 h. After the completion of reaction, the reaction mixture was concentrated in vacuo and the residue was partitioned between DCM (20 mL) and H2O (10 mL) and separated. The aqueous layer was re-extracted with DCM (3 X 15 mL) and the combined organic fractions were dried over anhydrous Na2SO4, filtered and concentrated in vacuo resulting in a crude product which was purified by preparative HPLC to afford 30 mg, (12 % yield ) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): = 8.26- 8.15 (m, 2H), 7.78 (t, J = 8.8 Hz, 2H), 7.50- 7.31 (m, 10H), 6.89- 6.80 (m, 2H), 4.47- 4.40 (m, 2H) , 4.06 – 3.85 (m, 4H), 3.36- 3.05 (m, 8H), 2.52 (s, 6H), 1.80- 1.60 (m, 4H), 1.40- 1.21 (m, 12H), 1.06 (t, J = 7.2 Hz, 6H); MS (ES+): m/z = 958.65, 960.70 [M+H] +; LCMS: tR = 3.3 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,10-Diiododecane, its application will become more common.

Reference:
Patent; COFERON, INC.; ARNOLD, Lee, Daniel; FOREMAN, Kenneth, W.; JIN, Meizhong; WANNER, Jutta; WERNER, Douglas, S.; WO2015/81284; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 21740-00-1, name is 5-Bromo-2-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 21740-00-1, Application In Synthesis of 5-Bromo-2-iodobenzoic acid

Concentrated H2S04 (10 mL) was added dropwise to the solution of 5- bromo-2-iodobenzoic acid (100 g, 305.89 mmol) in MeOH (800 mL). The mixture was refluxed for 16 hours and then concentrated. The residue was dissolved in ethyl acetate (1 L). The organic layer was washed with saturated NaHCO3 and brine (3 x 200 mL), dried over Na2SO4, filtered and concentrated to afford targetproduct 5-Bromo-2-iodo-benzoic acid methyl ester (101.4 g, yield 90%) as yellow solid.LC purity: 98.91 % (254 nm); Mass: find peak 341 (M + H)+ at 2.214 mm.

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; SANOFI; PASCAL, Cecile; PELLET, Alain; COURTEMANCHE, Gilles; CAMPBELL, Simon; (78 pag.)WO2019/8027; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com