Tag: M.W=300-400

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. 148870-57-9, name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, A new synthetic method of this compound is introduced below., Product Details of 148870-57-9

Based on EP 0 534 859 A solution of the (d) camphorsulphonate salt obtained in Example 4 in ethyl acetate is brought to basic pH using sodium hydroxide and then the organic phase is separated off, washed, dried over Na2SO4 and evaporated. A mixture composed of 5.6 g of potassium carbonate, 2.2 g of the above amine in 100 mL of acetone and 4 g of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is then refluxed for 18 hours. The solvent is evaporated off in vacuo, and the residue is taken up in ethyl acetate and then extracted with 3N hydrochloric acid. The aqueous phase separated off is brought to basic pH using sodium hydroxide and is then extracted with ethyl acetate. After washing until neutral and drying over MgSO4, evaporation in vacuo is carried out to obtain 4.5 g of an oil which is purified on a silica column using a mixture of dichloromethane/methanol (90/10) as eluant. Yield=64%

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; LES LABORATOIRES SERVIER; CARRANZA, Maria Del Pilar; GARCIA ARANDA, Maria Isabel; GONZALEZ, Jose Lorenzo; SANCHEZ, Frederic; US2014/107334; (2014); A1;,
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. 289039-83-4, name is Methyl 2-amino-5-bromo-3-iodobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 2-amino-5-bromo-3-iodobenzoate

To a solution of methyl 2-amino-5-bromo-3-iodobenzoate (7.47 g, 20.99 mmol) in TEA (40 mL, 287 mmol) is added Pd(PPh3)2C12 (0.884 g, 1 .259 mmol), and copper(l) iodide (0.240 g, 1.259 mmol). The mixture is stirred under N2 for about 5 mm, and then trimethylsilylacetylene (3.83 mL, 27.3 mmol) is added. The mixture is stirred at rt for I h. The reaction is followed by LCMS (only 6% product after I h). The mixture is then transferred to a pressure tube and additional Pd(PPh3)2C12 (0.14 g, 0.199 mmol) and copper(l) iodide (0.036 g, 0.189 mmol) are added. The mixture is purged with N2 for 1 mm, and then it is heated at 60 C for 2 h (LCMS shows 54% mono-alkyne and 35% bis-alkyne). The reaction mixture is concentrated under reduced pressure. The residue is taken up in CH2CI2 and filtered through a plug of Celite. The Celite plug is washed with CH2CI2. The filtrate is washed with water (2x) and brine (lx), dried over Na2SO4, filtered and concentrated. The residue is chromatographed over silica gel (120 g ISCO column) eluting with 0-5% EtOAc/hexane gradient to yield a mixture of methyl 2-amino-5- bromo-3-((trimethylsilyl)ethynyl)benzoate and methyl 2-amino-3, 5- bis((trimethylsilyl)ethynyl)benzoate (4.2 to I ratio by I H NMR). LCMS (ES API) MH+ = 326 & 328 for Br isotopes mono-alkyne product; and LCMS (ES API) MH+ = 344 bis-alkyne product.A mixture of methyl 2-amino-5-bromo-3-((trimethylsilyl)ethynyl)benzoate (500 mg, 1 .53mmol; contaminated with 20% of methyl 2-amino-3,5-bis((trimethylsilyl)ethynyl)benzoate) and2 eq of Cul (584 mg, 3.07 mmol) in DMF (4 mL) is set under N2 and heated in a sealed tube at100 C for 80 mm. Upon cooling, the reaction mixture is diluted with Et20 and filtered through aplug of Celite. The Celite plug is washed with Et20 and EtOAc. The filtrate is concentrated underreduced pressure. The residue is chromatographed over silica gel eluting with 0-15% EtOAchexane gradient to give the title compound as a light yellow solid. LCMS (ES API) MH+ = 254 &256 for Br isotopes.

The synthetic route of 289039-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BECHERER, J. David; CADILLA, Rodolfo; DEATON, David Norman; HAFFNER, Curt; HENKE, Brad Richard; PREUGSCHAT, Frank; SCHULTE, Christie; (69 pag.)WO2016/87975; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 63279-58-3, 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. 63279-58-3 name is 1-Bromo-4-iodonaphthalene, 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 I-AAThe mixture of 1-bromo-4-iodonaphthalene (I-IVb) (6.00 g, 18.01 mmol), 4-methoxyphenylboronic acid (2.74 g, 18.01 mmol), Na2CO3 (3.82 g, 36.02 mmol) and Pd(dppf)Cl2 (658 mg, 0.90 mmol) in 50 mL of THF and 10 mL of H2O was heated to reflux under argon overnight. The mixture was concentrated, the residue was partitioned between H2O and DCM, the aqueous phase was extracted with DCM. The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The residue was purified by chromatography on silica gel to afford 1-bromo-4-(4-methoxyphenyl)naphthalene (I-IVd) (4.50 g, yield 63percent).

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

Reference:
Patent; InterMune, Inc.; US2011/152246; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 181765-86-6, 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 181765-86-6 as follows.

In FIG. 1A, a chemical reaction, 101, is provided for the formation of methyl 5-bromo-2-trimethylsilylethynyl-benzoate using methyl 5-bromo-2-iodo-benzoate as a starting material. In this reaction, Sonogashira cross-coupling of trimethylsilyl (TMS) acetylene is such that the iodine of methyl 5-bromo-2-iodo-benzoate is replaced with trimethylsilylethyne (TMS) acetylene. For example, in one embodiment, in chemical reaction 101, TMS acetylene is reacts with methyl 5-bromo-2-iodo-benzoate in the presence of a palladium catalyst, for example bis-(triphenylphosphine)-palladium(II) dichloride, denoted Pd(PPh3)2 in FIG. 1A, and a copper catalyst, such as copper iodide, denoted CuI in FIG. 1A, using a deoxygenated solvent or solvent mixture that includes an organic amine, for example 1:1 dimethylformamide (DMF)/diethylamine (Et2NH) solvent solution, at 25 C. Upon completion, the solvent may be removed in vacuo, and the resulting slurry may be purified further by either standard aqueous workup conditions or filtration conditions. The crude product may be purified by recrystallization, column chromatography or by a variety of techniques known to those skilled in the art.

According to the analysis of related databases, 181765-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; International Business Machines Corporation; Kobilka, Brandon M.; Kuczynski, Joseph; Porter, Jacob T.; Wertz, Jason T.; (17 pag.)US2017/331044; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 182056-39-9, A common heterocyclic compound, 182056-39-9, name is 2-Bromo-4-iodo-1-methoxybenzene, molecular formula is C7H6BrIO, 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.

At -100 C., 1 mmol of nBuLi (1 eq.) is added to a solution containing 1 mmol of 2-bromo-4-iodo-1-methoxy-benzene dissolved in 15 mL of distilled hexane. After 45 minutes of stirring at this temperature, 0.5 mmol of 3,4,5-trimethoxyacetophenone diluted in 5 ml of distilled toluene is added. This mixture is stirred for hours while letting the temperature rise up gradually and is then slowly hydrolyzed by a saturated NH4Cl solution up to a pH=7-8. After extraction with diethylether (3×20 mL), the collected organic phases are dried on Na2SO4 and concentrated in the rotary evaporator. The raw reaction product is taken up in 10 mL of CH2Cl2 to which a few grains of hydrated APTS is added, and then stirred for 3 hours at room temperature. The solution is washed with a saturated NaCl solution, extracted with CH2Cl24. After drying on Na2SO4 and concentration in the rotary evaporator, an oil is collected which is purified on silica gel. Yield 53%.H1 NMR: delta ppm, CDCl3 300 MHz: 3.65 (s, 3H), 3.78 (s, 6H), 3.85 (s, 3H), 5.30 (s, 1H), 5.70 (s, 1H), 6.50 (s, 2H), 6.80 (d, 1H, J=8.7 Hz), 7.36-7.46 (m, 2H). Mass spectroscopy (ESI) [M+Na]+=403. Elemental analysis: (MM=378.05) Calculated C, 57.01; H, 5.05. Found C, 56.78; H, 4.90.

The synthetic route of 182056-39-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS); US2010/129471; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 689291-89-2, 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. 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: (5-Bromo-2-iodo-benzyl)-ethyl-amine To 5-bromo-2-iodo-benzaldehyde (5.0 g, 16.1 mmol) in MeOH (20 mL) was added ethylamine (2M in MeOH; 16 mL, 24.0 mmol), followed by acetic acid (1.0 mL, 17.8 mmol), and the mixture was stirred at room temperature for 30 minutes. Sodium cyanoborohydride (2.0 g, 31.8 mmol) was then added over 5 minutes, and the reaction was stirred at room temperature over the weekend. The mixture was concentrated and partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give the title compound.

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, 5-Bromo-2-iodobenzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; US2009/197959; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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

In a 500-mE round-bottom flask reactor, methyl5-bromo-2-iodobenzoate (25.0 g, 73 mmol), 4-dibenzofuran boronic acid (18.7 g, 88 mmol), tetrakis (triphenylphosphine)palladium (1.7 g, 0.15 mmol), and potassium carbonate (20.2 g, 146.7 mmol) were stirred together with toluene (125 mE), tetrahydrofuran (125 mE), and water (50 mE) for 10 hrs at 80 C. Afier completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer thus formed was separated, concentrated in a vacuum, and purified by column chromatography to afford . (75.0 g, 60.1%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 181765-86-6, its application will become more common.

Reference:
Patent; SFC CO., LTD.; KIM, Hee-Dae; PARK, Seok-Bae; SHIN, Yoona; LEE, Yu-Rim; PARK, Sang-Woo; CHA, Soon-Wook; (81 pag.)US2017/342318; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 34270-90-1 as follows. SDS of cas: 34270-90-1

Ethyl 2-(5-chloro-6-(2,2,2-lrifluoroethoxy)-4′-(lTifluoromethyl)biphenyl-3- y])acetate (0.4 g, 3.4 mrao) was dissolved in anhydrous DMF (30mL), NaH (60% wt. in paraffin oil, 0,163 g, 6.8 rnmol) was added at 0C. The reaction mixture was stirred for 30 rnin at room temperature and l-iodo-2-(2-iodoethoxy)ethane (1.2 g, 3.7 rnmol) was added drop wise at 0 C. The reaction mixture was stirred an additional 1h at 0 C and saturated NH4C1 solution (lOmL) was added. The reaction mixture was extracted with EtOAc (3x20mL) and the combined organic phases were washed with water (3x20mL) and brine (20mL), and dried over MgS04. The volatiles were removed under reduced pressure and the residue was purified by flash column chromatography to yield ethyl 4-(5-chloro-6- (2,2,2-trifiuoroethoxy)~4′-(trifluorornecarboxylate (400 mg).

According to the analysis of related databases, 34270-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; KOENIG, Gerhard; BLAIN, Jean-francois; WO2013/106328; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 148870-57-9, 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. 148870-57-9 name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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 6 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one Based on EP 0 534 859 A solution of the (d) camphorsulphonate salt obtained in Example 5 in ethyl acetate is brought to basic pH using sodium hydroxide and then the organic phase is separated off, washed, dried over Na2SO4 and evaporated. A mixture composed of 5.6 g of potassium carbonate, 2.2 g of the above amine in 100 mL of acetone and 4 g of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is then refluxed for 18 hours. The solvent is evaporated off in vacuo, and the residue is taken up in ethyl acetate and then extracted with 3N hydrochloric acid. The aqueous phase separated off is brought to basic pH using sodium hydroxide and is then extracted with ethyl acetate. After washing until neutral and drying over MgSO4, evaporation in vacuo is carried out to obtain 4.5 g of an oil which is purified on a silica column using a mixture of dichloromethane/methanol (90/10) as eluant. Yield=64%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Les Laboratoires Servier; Vaysse-Ludot, Lucile; Le Flohic, Alexandre; Vaultier, Michel; Pucheault, Mathieu; Kaminski, Thomas; US8859763; (2014); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 175278-11-2, These common heterocyclic compound, 175278-11-2, name is 1-Bromo-3,5-difluoro-2-iodobenzene, 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.

Step 3. Ethyl 2-(2′-bromo-4′,6′-difluoro-2,3,4,5-tetrahydro-[l,l’-biphenyl]-4-yl)acetate. In a sealed microwave tube, a mixture of ethyl 2-[4-(tetramethyl-l,3,2-dioxaborolan-2- yl)cyclohex-3-en-l-yl] acetate (200 mg, 0.68 mmol), [1,1′- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (24.9 mg, 0.03 mmol), l-bromo-3,5- difluoro-2-iodobenzene (260 mg, 0.82 mmol) and sodium carbonate (0.85 mL, 2.0 M, 1.7 mmol) in dioxane (3.40 mL) was heated at 70C for 20 h. Upon completion of the reaction, the reaction mixture was filtered through celite, washed thoroughly with EtOAc, and purified via flash chromatography (0-20% EtOAc/heptanes) to obtain the title compound as a colorless oil (210 mg, 86%). 1H NMR (400 MHz, CDCb) d 7.13 (td, /= 2.0, 8.1 Hz, 1H), 6.78 (dt, / = 2.5, 8.8 Hz, 1H), 5.60 (d, / = 1.7 Hz, 1H), 4.17 (q, / = 7.2 Hz, 2H), 2.45 – 2.31 (m, 3H), 2.22 – 2.12 (m, 1H), 2.00 – 1.84 (m, 2H), 1.63 – 1.50 (m, 1H), 1.48 (s, 2H), 1.28 (t, / = 7.1 Hz, 3H). [M+H] = 361.0.

Statistics shows that 1-Bromo-3,5-difluoro-2-iodobenzene is playing an increasingly important role. we look forward to future research findings about 175278-11-2.

Reference:
Patent; DART NEUROSCIENCE, LLC; BASINGER, THOMPSON, Jillian; BOOKSER, Brett; BURLEY, Scott; GARCIA-REYNAGA, Pablo; HUDSON, Andrew; PETERS, Marco; PRATT, Benjamin; THOMPSON, Aaron; TRAN, Joe; VALDEZ, Lino; (211 pag.)WO2019/168866; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com