Tag: M.W=300-400

Application of 98-61-3, 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. 98-61-3, name is 4-Iodobenzenesulfonyl chloride belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 100mL Schlenk tube, add 2.000g (30.5mmol) zinc powder, 3.0 ml dimethyldichlorosilane and 40 ml of 1,2-dichloroethane. Under the protection of nitrogen, use constant pressure dropping funnel to add dropwise 1.512g (5.0mmol) p-iodobenzenesulfonyl chloride, 1.5 ml of N,N-dimethylacetamide and 40 ml of 1,2-dichloroethane mixuture solution. Heat to 75 deg.C and react until zinc powder disappears. Then reduce the temperature to room temperature. Then add 10.0 ml of pyridine. Under stirring, add 5.0 ml (35.0mmol) acetyl chloride. Continue stirring at room temperature under nitrogen protection for 18h. After the reaction, filtration, washing, removing the solid, the filtrate drying, mixed with petroleum ether and ethyl acetate filtrate (150 : 1v/v) as developing solvent, chromatography column for separation, the spin vaporization of solvent, dried under vacuum to get the 1.3502g white solid, i.e., acetic acid-4-iodo thiophenol ester. Yield 97.1%.

The synthetic route of 4-Iodobenzenesulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liaoning University; Xia, Lixin; Li, Haihua; Wang, Jing; Zhang, Qian; Song, Peng; (10 pag.)CN105669507; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 391211-97-5, name is 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic 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 391211-97-5, COA of Formula: C13H7F3INO2

A solution of 3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzoic acid (201 mg, 0.512 mmol), prepared using procedures similar to those described in US 7,019,033, 3-(2- aminopyrimidin-4-yl)azetidin-3-ol (87 mg, 0.52 mmol), benzotriazol-1-yl-oxy- tris(pyrrolidino)phosphonium hexafluorophosphate (293 mg, 0.563 mmol) and MN-diisopropylethylamine (270 uL, 2.82 mmol) in N,jV-dimethylformamide (2 mL) was stirred at room temperature for 2Oh. The mixture was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was separated and washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by reverse phase HPLC to afford the title compound 3-(2-aminopyrimidin-4-yl)-l-({3,4- difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)azetidin-3-ol (22 mg, 7%). 1H NMR (400 MHz, CD3OD): 8.23-8.20 (d, IH), 7.48-7.43 (d, IH), 7.35-7.32 (m, 2H), 7.09- 7.00 (m, IH), 6.88-6.84 (d, IH), 6.70-6.63 (t, IH), 4.59-4.54 (d, IH), 4.45-4.40 (d, IH), 4.23- 4.18 (d, IH), 3.04-3.99 (t, IH); MS (EI) for C20H15F3IN5O2: 542 (MH+).

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, 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EXELIXIS, INC.; WO2008/124085; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 181765-86-6, A common heterocyclic compound, 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, molecular formula is C8H6BrIO2, 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.

To a stirred solution of sodium borohydride (1 .1 g, 14.7 mmol, 2 equiv) in ethanol (20 mL) was added methyl 5-bromo-2-iodobenzoate in THF (10 mL) at 5C. The reaction mixture was warmed to room temperature and stirred for 18 h under nitrogen atmosphere. Additional quantity of sodium borohydride (0.84 g, 22 mmol, 1 .5 equiv) was added and the mixture was stirred for 22 h. The reaction mixture was cooled to 0C, treated with 10 mL of 15% citric acid slowly. The reaction mixture was extracted with DCM (2 x 75 mL). The organic layer was washed with 15% of aq. NaCI (100 mL), and then dried over sodium sulphate and evaporated to obtain (5-bromo-2-iodophenyl)methanol (4.5 g, 100%) as white solid. NMR (400 MHz, CDCI3) delta ppm 1 .83 – 1 .88 (m, 1 H), 4.63 (s, 2H), 7.12 (dd, J=2.8, 8.4 Hz, 1 H), 7.62- 7.66 (m, 2H).

The synthetic route of 181765-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; KETHIRI, Raghava Reddy; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (162 pag.)WO2018/15879; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 689260-53-5, name is 2-Bromo-5-iodo-1,3-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 689260-53-5, category: iodides-buliding-blocks

the obtained 38-6-a (3.92 g, 20 mmol), Bis(pinacolato)diboron (6.22 g, 24 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.49 g, 0.6 mmol), potassium acetate (5.90 g, 60 mmol) and 79 ml of toluene were reacted under reflux for 16 hours.After cooling, 26 ml of water was added and stirred for 30 minutes, the organic phase was separated, filtered through a short bed of celite, soon afterwards the organic solvent was evaporated off, and the obtained crude product was recrystallized from heptane / toluene; Under argon atmosphere, the obtained solid 38-6-b (3.65g, 15mmol), 38-6-c (4.45g, 14.3mmol), Tetrakis(triphenylphosphine)palladium (0·35 g, 0.3 mmol), toluene (43 ml), aqueous sodium carbonate (2M, 21 ml) was added to the flask and refluxed for 8 hours.After cooling to room temperature, it was extracted with toluene, and the organic phase was washed with brine, and then dried, and then purified by column chromatography to obtain bromide 38-6-d; Tri-tert-butylphosphine (4.4 mL of a 1.0 M solution in toluene, 1.48 g, 0.05 mmol), palladium acetate (0.4 g, 1.83 mmol) and sodium tert-butoxide (52.7 g, 549 mmol) were added to a solution of 38-6-d (22.04 g, 73.42 mmol) and bromobenzene (11.53 g, 73.42 mmol) in degassed toluene (500 mL) and the mixture was Heat under reflux for 2 hours. This reaction mixture was cooled to room temperature, diluted with toluene and filterated through celite. This filtrate was diluted with water and extracted with toluene, and the organic phases were combined and evaporated in vacuo. This residue was filtered through silica gel (heptane / dichloromethane) and crystallised from isopropyl alcohol to give compound 38-6-e;the obtained 38-6-a (3.92 g, 20 mmol), Bis(pinacolato)diboron (6.22 g, 24 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (0.49 g, 0.6 mmol), potassium acetate (5.90 g, 60 mmol) and 79 ml of toluene were reacted under reflux for 16 hours.After cooling, 26 ml of water was added and stirred for 30 minutes, the organic phase was separated, filtered through a short bed of celite, soon afterwards the organic solvent was evaporated off, and the obtained crude product was recrystallized from heptane / toluene to obtain compound 38-6.

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-Bromo-5-iodo-1,3-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Zhang Hong; Cai Hui; (28 pag.)CN108530336; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 328-73-4,Some common heterocyclic compound, 328-73-4, name is 1-Iodo-3,5-bis(trifluoromethyl)benzene, molecular formula is C8H3F6I, 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.

The compound represented by the formula (1d) was synthesized by the following method.First, in the four-necked flask purged with argon by the following procedure,3,5-dibromo-2-cyclohexyloxythiophene[Document description: K.K. Morimitsu, K.M. Shibata, S. Kobatake, M.M. Irie, J.M. Org. Chem. , 67, 4574-4578 002)] 1.2 g (3.4 mmol)Dissolve in 60 mL of anhydrous tetrahydrofuran,Cooled to -80 C. 1.6 M n-butyllithium hexane solution 2.4 mL (3.8 mmol) was slowly added dropwise,Stir for 1 hour. Next, tributyl borate 1.1 mL(4.1 mmol) was slowly added dropwise and stirred for 1 hour.Add water to stop the reaction, return to room temperature,3,5-bis (trifluoromethyl) iodobenzene 1.2 g (3.4 mmol), Pd (PPh3) 4 80 mg,Add 6.0 mL of 20 wt% sodium carbonate aqueous solution,The set temperature of the oil bath was 80 C. and refluxed for 7 hours.After returning to room temperature, neutralize with dilute hydrochloric acid,Extracted with diethyl ether.After washing the organic layer with saturated aqueous sodium chloride solution,Add magnesium sulfate and dry,The magnesium sulfate was removed by filtration and concentrated.Then, it isolate | separates by silica gel column chromatography (Rf = 0.3) using hexane as a developing solvent, and HPLC.(Developing solvent: hexane)Yield 1.1g, Yield 66%

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

Reference:
Patent; Osaka City University; Obata, Makoto; (25 pag.)JP2019/151632; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 98-61-3, 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. 98-61-3, name is 4-Iodobenzenesulfonyl chloride belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A aqueous solution (15mL) containing 4mmol of corresponding sulfonyl chloride, 4mmol of sodium sulfite, 4mmol of sodium hydrogenocarbonate and 2mmol corresponding 2-chloromethylated imidazo[1,2-a]pyridines was heated under microwave irradiation (120C, 5bars) in a sealed vial. After disappearance of the starting materials (about 1h), monitored by TLC, the solid was collected by filtration and dried under reduced pressure to give, after purification by column chromatography on silica gel and/or recrystallization, the expected product in 25-100% yield.

The synthetic route of 4-Iodobenzenesulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Castera-Ducros, Caroline; Paloque, Lucie; Verhaeghe, Pierre; Casanova, Magali; Cantelli, Christophe; Hutter, Sebastien; Tanguy, Floriane; Laget, Michele; Remusat, Vincent; Cohen, Anita; Crozet, Maxime D.; Rathelot, Pascal; Azas, Nadine; Vanelle, Patrice; Bioorganic and Medicinal Chemistry; vol. 21; 22; (2013); p. 7155 – 7164;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 31827-94-8, 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. 31827-94-8 name is 2-Bromo-1-(4-iodophenyl)ethanone, 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.

Example 32B 2-[2-(4-Iodo-phenyl)-2-oxo-ethyl]-malonic Acid Diethyl Ester Under N2, diethyl malonate (Aldrich, 8.0 g, 50 mmol) was treated with sodium hydride (1.2 g, 50 mmol) in dry THF (120 mL) at 0′ C. for 30 minute. The solution of the product of Example 32A (15.8 g, 48.6 mmol) in THF (30 mL) was then slowly added at 0′ C. and the reaction mixture stirred additional 30 minutes at room temperature. It was quenched with water (10 mL) carefully and diluted with ethyl acetate (200 mL). The mixture was then washed with brine (3*20 mL). The organic solution was concentrated to give the title compound as oil (15 g, 74%). 1H NMR (300 MHz, CDCl3) delta 1.25-1.32 (m, J=7.1, 7.1 Hz, 7H), 3.57 (d, J=7.1 Hz, 2H), 4.16-4.29 (m, 4H), 7.69 (d, J=8.5 Hz, 2H), 7.84 (d, J=8.8 Hz, 2H) ppm; MS (DCl/NH3) m/z 405 (M+H)+, 422 (M+NH4)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-(4-iodophenyl)ethanone, and friends who are interested can also refer to it.

Reference:
Patent; Abbott Laboratories; US2005/159597; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 628-77-3, 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. 628-77-3 name is 1,5-Diiodopentane, 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.

Compound 259a:[332] In a smal] vial dissolved Compound 8 (0.100 g, 0.340 mmol) in DMF (5 ml) with stirring at room temperature. 1,5-diiodopentane (0.506 ml, 3.40 mmol) was added fol]owed by the addition of potassium carbonate (0.070 g, 0.510 mmol). The reaction was covered in foil and stirred at room temperature overnight. The reaction was diluted with dichloromethane and washed with aqueous ammonium chloride and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica ptlc using 50% ethyl acetate in hexane to give Compound 259a (0.045 g, 7.32 mumol, 27 % yield). 1H NMR (400 MHz, CDCl3): delta 1.64 (m, 2H), 1.94 (M, 4H), 3.24 (t, 2H, J = 6.5 MHz), 3.52 (dd, IH, J = 4.0, 16.6 MHz), 3.73 (dd, IH, J = 10.5, 16.6 MHz), 3.98 (s, 3H), 4.12 (m, 2H), 4.50 (dt, IH, J = 4.0, 11.2 MHz), 6.84 (s, IH), 7.13 (t, IH, J = 6.0 MHz), 7.29 (m, 2H), 7.57 (s, IH), 7.90 (d, IH, J = 4.4 MHz), 8.29 (d, IH, J = 8.0 MHz). MS (m/z), found 533.3 ([M]++K).

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

Reference:
Patent; IMMUNOGEN, INC.; LI, Wei; FISHKIN, Nathan, Elliott; ZHAO, Robert, Yongxin; MILLER, Michael, Louis; CHARI, Ravi, V., J.; WO2010/91150; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, molecular formula is C7H4BrIO, 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. name: 5-Bromo-2-iodobenzaldehyde

EXAMPLE 112b Preparation of intermediate 1-(2-iodo-5-bromo-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene To dry tetrahydrofuran (120 mL) was added a solution of LiHMDS (42 mmol, 42 ml) in THF under argon at room temperature, followed by the addition of 5-bromo-2-iodo-benzaldehyde (13 g, 42 mmol). After the mixture was stirred at room temperature for 0.5 h, trimethylsilyl chloride (5.32 mL, 42 mmol) was added dropwise. Then the temperature of the mixture was lowered to 0 C. on a cooling ice bath. To this mixture was added triethylamine (7.6 mL, 54.4 mmol) in one portion, followed by the dropwise addition of a solution of acetyl chloride (3.9 mL, 54.4 mmol) in diethyl ether (200 mL). The cooling bath was removed, and the mixture was stirred at room temperature for 1 h. The mixture was quickly filtered on celite under nitrogen, and filtrate was concentrated under reduced pressure to give the title compound as a yellow gum and used for the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 689291-89-2, its application will become more common.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Yang, Song; Zhang, Jing; Zhang, Zhuming; US2009/156610; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 61203-48-3,Some common heterocyclic compound, 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, molecular formula is C9H9IO4, 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.

[C.] [N- (6-NITROQUINOLIN-4-YL)-N- (N, N-DIMETHYLAMINOETHYL)-2-IODO-5,] 6- dimethoxybenzamide (8c). Oxalyl chloride (1.5 g, 12.0 mmol) was added to a solution of 3, 4-dimethoxy-6-iodobenzoic acid (985 mg, 3.2 mmol) in anhydrous methylene chloride (20 mL), and the stirred mixture was refluxed for 3 hours. The mixture was then concentrated to dryness under reduced pressure. The acid chloride was redissolved in 20 mL of anhydrous methylene chloride, and this solution was added to a solution of 7c (700 mg, 2.7 mmol) and triethylamine (2.0 g, 20.0 mmol) in methylene chloride (30 mL), and the resulting mixture was stirred at reflux for 2 hours. The reaction mix was cooled and washed with saturated sodium bicarbonate (3 x 75 mL), and extracted with 5 % aqueous HCl (4 x 100 mL). The combined aqueous extracts were basified with 30% [NAOH] and then extracted with chloroform (3 x 100 mL). Combined organic extracts were then dried [(MGSO4)] and evaporated to give 1.15 g of the amide, in 78 % yield ; 1H NMR [(CDC13)] 8 2.23 (s, 6H), 2.63 (m, 2H), 3.35 (s, 3H), 3.71 (s, 3H), 3.96 [(M,] 1H), 4.29 (m, 1H), 6.50 (s, 1H), 6.94 (s, [1H),] 7.79 (d, 1H, [J=5.] 2), 8.22 (d, [1H,] [J=9.] 2), 8. 48 (d, 1H, J=9. 2), 9.0 (d, 1H, J=5. 2), 9.28 (s, [1H)] ; [13C] NMR [(CDC13)] [5] 45.5, 48.0, 55.6, 56.1, 56. 8, 82.3, 110.7, 120.9, 121.5, 122.9, 123.4, 125.5, 132.2, 133.7, 145.9, 148.4, 149.1, 149. 8, 151.5, 154.1, 169.7 ; IR (CHC13) 1345,1535, 1655.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodo-4,5-dimethoxybenzoic acid, its application will become more common.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY; LAVOIE, Edmond, J.; RUCHELMAN, Alexander, L.; LIU, Leroy, F.; WO2004/14906; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com