Tag: M.W=300-400

These common heterocyclic compound, 391211-97-5, name is 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, 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. Recommanded Product: 391211-97-5

To a flask containing 3, 4-difluoro-2- (2-fluoro-4-iodo-phenylamino)-benzoic acid (2.6 Kg, 6.6 mol) and N, N’-carbonyldiimidazole (1.1 Kg, 6.8 mol) under nitrogen atmosphere, was added 12 L of dry acetonitrile. After stirring at 22 5C for about 90 minutes, a solution of (R)-O- (2, 2-dimethyl- [1, 3] dioxolan-4-ylmethyl)-hydroxylamine in toluene was added (8.5 L total volume, about 8 moles of amine). The solution was stirred for at least 6 hours at 22 5 C. Aqueous hydrochloric acid (9 L, 1.5 molar) was added, and after stirring for about 5 minutes, the layers were separated. Aqueous hydrochloric acid (9 L, 1.5 molar) was added to the remaining top layer, and after stirring for about 20 hours, the layers were separated. The remaining top layer was concentrated by vacuum distillation, and then diluted with 15 L toluene and 2 L ethanol. The mixture was warmed to 35-45C and diluted with 20 L warm water, then cooled to 0-5C. The product was collected by filtration and washed with 2 L toluene. The product was recrystallized by dissolving in 12 L toluene and 2 L ethanol (50 5 C), adding 10 L water and cooling to 0-5C. After collecting the product by filtration and washing with toluene, the product was dried in a vacuum oven resulting in 2.6 Kg of N-[(R)- 2,3-Dihydroxypropoxy]-3, 4-difluoro-2- (2-fluoro-4-iodo-phenylamino)-benzamide. 2.4 Kg of the above compound as a mixture of different crystalline forms was stirred in a mixture of 10 L water and 1 L ethanol at 35+ 5C for 20-30 hours, then cooled to 25+ 5C. The product was collected by filtration and washed with 1 L of water, then dried in a vacuum oven at 65C. This resulted in 2.3 Kg of material which was greater than 90% form IV. Note: DSC analysis shows an onset of melting at 110C with only a small amount of the peak with an onset of melting at 117C.

The synthetic route of 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/46665; (2005); A1;,
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Application of 915095-86-2,Some common heterocyclic compound, 915095-86-2, name is (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone, molecular formula is C13H7ClFIO, 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 solution of the fluoride VIII.1 (208 kg), tetrahydrofuran (407 kg) and (S)-3-hydroxytetrahydrofuran (56 kg) is added potassium-tert-butanolate solution (20percent) in tetrahydrofuran (388 kg) within 3 hrs at 16 to 25¡ã C. temperature. After completion of the addition, the mixture is stirred for 60 min at 20¡ã C. temperature. Then the conversion is determined via HPLC analysis. Water (355 kg) is added within 20 min at a temperature of 21¡ã C. (aqueous quench). The reaction mixture is stirred for 30 min (temperature: 20¡ã C.). The stirrer is switched off and the mixture is left stand for 60 min (temperature: 20¡ã C.). The phases are separated and solvent is distilled off from the organic phase at 19 to 45¡ã C. temperature under reduced pressure. 2-Propanol (703 kg) is added to the residue at 40 to 46¡ã C. temperature and solvent is distilled off at 41 to 50¡ã C. temperature under reduced pressure. 2-Propanol (162 kg) is added to the residue at 47¡ã C. temperature and solvent is distilled off at 40 to 47¡ã C. temperature under reduced pressure. Then the mixture is cooled to 0¡ã C. within 1 hr 55 min. The product is collected on a centrifuge, washed with a mixture of 2-propanol (158 kg) and subsequently with tert.-butylmethylether (88 kg) and dried at 19 to 43¡ã C. under reduced pressure. 227 kg (91.8percent) of product are obtained as colourless solid. The identity of the product is determined via infrared spectrometry.

The synthetic route of 915095-86-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/237789; (2011); A1;,
Iodide – Wikipedia,
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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. 391211-97-5, name is 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 391211-97-5

EXAMPLE 50A N-[(S)-2,3-Dihydroxy-propoxy]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzamide (Form II of Compound C) Prepared from (S)-O-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine and 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzoic acid by the alternative procedure described above for N-[(R)-2,3-Dihydroxy-propoxy]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzamide: m.p. 118-119 C.

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; Barrett, Stephen Douglas; Biwersi, Cathlin Marie; Chen, Michael Huai Gu; Kaufman, Michael David; Tecle, Haile; Warmus, Joseph Scott; US2004/54172; (2004); A1;,
Iodide – Wikipedia,
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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. 199786-58-8, name is (5-Bromo-2-iodophenyl)methanol, A new synthetic method of this compound is introduced below., Application In Synthesis of (5-Bromo-2-iodophenyl)methanol

General procedure: A magnetic stirring bar, 2-iodobenzyl alcohol (1a, 116.0 mg, 0.5 mmol), NEt3 (251.6 mg, 2.5 mmol), and MeCN (10 mL) were placed in a stainless steel autoclave equipped with an inserted Pyrex glass liner. The autoclave was closed, purged three times with carbon monoxide, pressurized with 65 atm of CO and then heated at 250 C by salt bath with stirring for 16 h. After the reaction, excess CO was discharged at room temperature. The solvent was removed under reduced pressure, and the residue was purified by flash chromatography on silica gel (hexane/EtOAc = 3/1) to give 2a (60.4 mg, 91%) as a white solid.

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:
Article; Fukuyama, Takahide; Bando, Takanobu; Ryu, Ilhyong; Synthesis; vol. 50; 15; (2018); p. 3015 – 3021;,
Iodide – Wikipedia,
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Related Products of 1131614-23-7,Some common heterocyclic compound, 1131614-23-7, name is Methyl 4-(difluoromethoxy)-3-iodobenzoate, molecular formula is C9H7F2IO3, 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.

mixture of methyl 4-(difluoromethoxy)-3-iodobenzoate (2 g, 6.1 mmol) from step 1 , 2- ethynylpyridine (0.94 ml_, 9.2 mmol), dichlorobistriphenylphosphine palladium(ll) (0.86 g, 1.2 mmol), copper iodide (0.23 g, 1.2 mmol) and triethylamine (1.7 ml_, 12.2 mmol) in toluene (30 ml.) was stirred at 100 0C under an atmosphere of nitrogen for six hours. After the reaction was complete, the reaction mixture was concentrated to yield a semi-solid residue. This residue was purified by flash chromatography on SiO2 (gradient elution using EtOAc/hexane 20/80) to yield the title compound as a white solid (1.47 g, 80% yield).

The synthetic route of 1131614-23-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH LLC; LI, David, Zenan; O’NEIL, Steven, Victor; SPRINGER, Dane, Mark; ZEGARELLI, Benjamin, Miller; WO2010/124047; (2010); A1;,
Iodide – Wikipedia,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1258298-01-9 as follows. Recommanded Product: 2,6-Dichloro-4-iodobenzoic acid

Thionyl chloride (20 mL) was added to 2,6-dichloro-4-iodobenzoic acid (1.5 g, 4.73 mmol) and the mixture was heated to reflux for 5 h under nitrogen. After cooling the mixture was concentrated under reduced pressue. Toluene (10 mL) was added and the mixture was concentrated under reduced pressure again to remove residual thionyl chloride. The residue was dissolved in anhydrous THF (20 mL) and this was added dropwise to a cooled (0 C.) solution of 4-aminopyridine (0.53 g, 5.68 mmol) and triethylamine (1.32 mL, 9.46 mmol) in anhydrous THF (20 mL). After addition was complete, the mixture was stirred at room temperature under nitrogen overnight. The reaction was poured onto the ice water (50 mL) and extracted with EtOAc (2¡Á50 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hexanes/EtOAc=3:1) to afford the desired product (1.8 g, yield: 97%.) 1HNMR (DMSO-d6, 400 MHz): 611.14 (s, 1H), 8.47 (dd, J=1.6, 4.8 Hz, 2H), 8.03 (d, J=2.0 Hz, 2H), 7.59 (dd, J=1.6, 4.8 Hz, 2H). LCMS (ESI) m/z: 393.0 [M+H+].

According to the analysis of related databases, 1258298-01-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; US2010/317643; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 755027-18-0, 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. 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of l-bromo-4-iodo-2-methoxybenzene (L. A. Hasvold et al, US 2004/0254159, EXAMPLE 57B) (33.45 g, 107 mmol) in MeCN (100 mL) was added acrylic acid (9.61 g,, 133 mmol), Et3N (37.2 mL, 267 mmol) and palladium acetate (719 mg, 3.2 mmol). The reaction mixture was heated to 9O0C for 40 minutes, cooled to RT and poured into 2.4 L IM HCl. After stirring for 30 minutes, the solid was filtered, heated to reflux in EtOH (230 mL), allowed to cool to RT and stirred overnight. The solid was filtered and washed with 1 : 1 EtOH hexane (50 mL) to give desired product. LRMS ESI+ (M+H)+ 257.0.

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

Reference:
Patent; MERCK & CO., INC.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2008/51475; (2008); A2;,
Iodide – Wikipedia,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 791642-68-7 as follows. SDS of cas: 791642-68-7

2-Methylpyridine-4-boronic acid pinacol ester (5.49 g, 25.1 mmol) and Pd(PPh3)4 (3.62 g, 3.1 mmol) was added to a solution of intermediate 54 (9.8 g, 31.3 mmol) in dioxane (200 ml), H20 (50 ml) and K2CO3 (13 g, 94 mmol). The resulting mixture was stirred and heated at 100 C for 18 h. The r.m. was cooled to r.t. and partitioned between H20 and DCM. The combined organic layers were dried (MgS04), filtered and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel (eluent: DCM/MeOH from 100/0 to 98/4). The product fractions were collected and concentrated in vacuo, yielding 4.5 g of intermediate 55 (52 %).

According to the analysis of related databases, 791642-68-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; DE CLEYN, Michel, Anna, Jozef; VAN BRANDT, Sven, Franciscus, Anna; GIJSEN, Henricus, Jacobus, Maria; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; WO2011/86098; (2011); A1;,
Iodide – Wikipedia,
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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. 260355-20-2, name is 1-Chloro-4-iodo-2-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Safety of 1-Chloro-4-iodo-2-(trifluoromethyl)benzene

[Reference Example 1] 4-chloro-3-trifluoromethyl-1-(1-trifluoromethylethenyl) benzene In a nitrogen atmosphere, to 53 mL of a 1M tetrahydrofuran solution of 1-trifluoromethylethenyl zinc bromide prepared according to a method described in the literatures, 7.1 g of 2-chloro-5-iodobenzotrifluoride and 0.65 g of dichlorobis(triphenylphosphine) palladium (II) were added and the resultant mixture was stirred while heating the mixture to reflux for 2.5 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and 200 mL of hexane was added to the reaction mixture, followed by filtering off the deposited insoluble substance. The resultant filtrate was washed with water (50 mL*1) and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluding with hexane to obtain 4.8 g of the objective substance as a colorless oily substance. 1H NMR (CDCl3, Me4Si, 300 MHz) delta 7.75 (s, 1H), 7.57 (d, J=8.8 Hz, 1H), 7.54 (d, J=8.8 Hz, 1H), 6.08 (s, 1H), 5.84 (s, 1H).

The synthetic route of 260355-20-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nissan Chemical Industries, Ltd.; EP2199287; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 148870-57-9, The chemical industry reduces the impact on the environment during synthesis 148870-57-9, name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, I believe this compound will play a more active role in future production and life.

From 11 g of that product, 3.3 g of LiAlH4 and 160 ml of tetrahydrofuran heated at reflux for 6 hours, 7 g of N-[(4-methoxybenzocyclobut-1-yl)methyl)-N-(methyl)amine (yield 90%) are obtained. From 15 g of 7,8-dimethoxy-3-[3-iodopropyl]-1,3-dihydro-2H-3-benzazepin-2-one, 7 g of N-[(4-methoxybenzocyclobut-1-yl)methyl]-N-(methyl)amine, 22 g of K2 CO3 and 300 ml of acetone, there are obtained 17.5 g (theoretical yield) of 7,8-dimethoxy-3-{3-{N-[(4-methoxybenzocyclobut-1-yl)-methyl)-N-(methyl)amino}propyl}-1,3-dihydro-2H-3-benzazepin-2-one. From 5 g of that product, 60 ml of ethanol, 1 ml of acetic acid and 3 g of palladium hydroxide, there are obtained 1.9 g of 7,8-dimethoxy-3-{3-{N-[(4-methoxybenzocyclobut-1-yl)methyl]-N-(methyl)amino}propyl}-1,3,4,5-tetrahydro-2H-3-benzazepin.-2-one (yield: 65%), which is converted into the corresponding dihydrochloride which, recrystallized from acetonitrile, melts at 160-164 C.

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, 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Adir et Compagnie; US5296482; (1994); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com