Month: June 2021

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. 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H6BrIO2

In a 500-mL round-bottom flask reactor, methyl 5-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) stirred together with toluene (125 mL), tetrahydrofuran (125 mL), and water (50 mL) for 10 hrs at 80 C. After 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%).

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

Reference:
Patent; SFC CO., LTD.; Pyo, Sung-Wan; Shim, So Young; Yu, Se Jin; (133 pag.)US2017/12214; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 33348-34-4, name is 4-Amino-3-iodobenzonitrile, molecular formula is C7H5IN2, 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. category: iodides-buliding-blocks

General procedure: A solution of 2-iodoaniline (333.6 mg, 1.52 mmol, 1.0 equiv) in DCM (5.0 mL) was added with Et3N (0.23 mL, 166.9 mg, 1.65 mmol, 1.1 equiv). The reaction solution was cooled at 0 C and acetyl chloride (0.28 mL, 308 mg, 3.92 mmol, 2.6 equiv) was added into the cooled solution. The resulting mixture was warmed to stir at room temperature overnight. Upon completion, thereaction was added with water and the separated aqueous phase was extracted with EtOAc (3xtimes). The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30% EtOAc-hexane to yield 387.9 mg (98%) of the corresponding N-(2-iodophenyl)acetamide as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33348-34-4, its application will become more common.

Reference:
Article; Chaisan, Nattawadee; Kaewsri, Wilailak; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Ruchirawat, Somsak; Tetrahedron Letters; (2018); p. 675 – 680;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 13194-68-8, A common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, 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 solution of 4-iodo-2-methyl-aniline (200 mg, 858.19 mumol, 1 eq) and 2-methylpyrazole-3-carboxylic acid (129.87 mg, 1.03 mmol, 1.2 eq) in EtOAc (10 mL) was added T3P (1.64 g, 2.57 mmol, 1.53 mL, 50%, 3.0 eq) and DIEA (332.74 mg, 2.57 mmol, 448.44 muL, 3.0 eq). The mixture was stirred at 60 C. for 3 h. The mixture was stirred at 60 C. for 16 h. The reaction mixture was diluted with NaHCO3 solution (20 mL), extracted with ethyl acetate (20 mL*3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a residue which was purified on silica gel column chromatography (from PE/EtOAc=1/0 to 10/3, TLC: PE/EtOAc=3/1, Rf=0.49) to give the product of N-(4-iodo-2-methyl-phenyl)-2-methyl-pyrazole-3-carboxamide (100 mg, 284.34 mumol, 33.1% yield, 97.0% purity) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.69 (d, J=8.4 Hz, 1H), 7.63-7.56 (m, 2H), 7.53 (d, J=2.2 Hz, 1H), 7.45 (br s, 1H), 6.64 (d, J=2.0 Hz, 1H), 4.23 (s, 3H), 2.28 (s, 3H); ES-LCMS m/z 341.8 [M+H]+.

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; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 608-28-6, name is 2-Iodo-1,3-dimethylbenzene, molecular formula is C8H9I, 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. Quality Control of 2-Iodo-1,3-dimethylbenzene

General procedure: A vial was charged with an aryl halide (0.1 mmol), an aryl or alkylacetylene(0.11 mmol), K2CO3 (0.15 mmol), palladium catalyst (0.05 mol %), and EtOH(2 mL). The mixture was refluxed with stirring for 2 h. After this time, themixture was cooled and CH2Cl2-n-hexane (1:2, 2 mL) and H2O (2 mL) wereadded. The organic layer was separated, filtered through a small amount ofsilica gel and analyzed by GC-MS. The solvent was removed and the residueweighed and analyzed by 1H NMR.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 608-28-6, its application will become more common.

Reference:
Article; Savicheva, Elizaveta A.; Kurandina, Daria V.; Nikiforov, Vladimir A.; Boyarskiy, Vadim P.; Tetrahedron Letters; vol. 55; 13; (2014); p. 2101 – 2103;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 71838-16-9, 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. 71838-16-9 name is 2-Bromo-1-iodo-4-methylbenzene, 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.

The 170mg (1mmol) 5- chlorobenzothiazole, 534 (1.8mmol) 4- bromo-1-iodo-toluene, 12.5mg (0.05mmol) CuSO4·5H2O14mg(0.1mmol)L1690mg(5mmol)K2CO3, 2gPEG100, was added 10mL reaction tube, sealed, under the reaction condition of 80 14h.After the reaction was stopped, extraction with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, column chromatography was purified by silica gel column to give 2-chloro-8-methyl-phenothiazine piperazine 161mg, yield 65%.

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

Reference:
Patent; Sun Yat-sen University; Wan, Yiqian; Huang, Manna; Huang, Dongting; Zhu, Xinhai; (11 pag.)CN104529938; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 58313-23-8, name is Ethyl-3-iodobenzoate, molecular formula is C9H9IO2, 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: Ethyl-3-iodobenzoate

[6-(Methyloxy)-l-benzothien-2-yl]boronic acid (1.2 g, 5.77 mmol), ethyl-3- iodobenzoate (1.1 mL, 6.53 mmol), sodium carbonate (2 M) (6 mL, 12 mmol), tetrakis(triphenylphosphine)palladium(0) (0.241 g, 0.21 mmol), and toluene (30 mL) were combined and the stirred reaction mixture was heated at reflux for 3 h under a nitrogen atmosphere. The reaction mixture was allowed to stand at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was separated and extracted with ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give an oil. The crude product was purified by flash chromatography over silica with a hexanes:ethyl acetate gradient (100:0 to 95:5) to give 0.90 g (50%) of ethyl 3-[6-(methyloxy)-l-benzothien-2-yl]benzoate as a white solid. 1H NMR (400 MHz, DMSO-J6): delta 8.19 (s, IH), 8.00 (d, J = 8 Hz, IH), 7.90 (d, J = 8 Hz, IH), 7.87 (s, IH), 7.74 (d, J = 9 Hz, IH), 7.60 (t, J = 8 Hz, IH), 7.57 (d, J = 2 Hz, IH), 7.01 (dd, J = 9, 2 Hz, IH), 4.35 (q, J = 7 Hz, 2H), 3.82 (s, 3H), 1.33 (t, J = 7 Hz, 3H). ESI- LCMS m/z 313 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 58313-23-8, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/5998; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 52548-14-8, name is 2-Iodo-5-methylbenzoic 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 52548-14-8, COA of Formula: C8H7IO2

To a solution of 5-methyl-2-iodobenzoic acid (3.0 g, 11.4 mmol) in toluene (150 mL), SOCl2 (8.35 mL, 114 mmol) was added and the mixture was heated at 100 C. for 3 hours. The solvent was concentrated in vacuum and the residue was co-evaporated from toluene twice to give the title compound as a grey solid. Yield (3.2 g, 100%) [0180] 1H NMR (400 MHz, CDCl3): delta 2.42 (s, 3H), 7.09 (dd, 1H), 7.90 (d, 1H), 7.92 (d, 1H).

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-Iodo-5-methylbenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Stasi, Luigi Piero; Rovati, Lucio Claudio; US2015/65523; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 31599-60-7,Some common heterocyclic compound, 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, molecular formula is C8H9I, 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.

Example X 4-n-Butyl-1-[4-(2,3-dimethylphenyl)-4-oxo-1-butyl]piperidine (19) In a 10 mL oven-dried flask was added Mg turnings (94 mg, 3.8 mmol) which was activated under vacuum by the use of a heat-gun. Under inert atmosphere was added a suspension of 1-iodo-2,3-dimethylbenzene (0.69 g, 3.0 mmol) in Et2O (5 mL) under spontaneously reflux, and the reaction mixture was allowed to reflux for 4 hours. A suspension of compound 4 (0.41 g, 2.0 mmol) in CH2Cl2 (2 mL) was added to the reaction mixture and left at rt overnight. The reaction mixture was quenched by addition of H2SO4 (7 mL, 2 M) and stirred at rt for 3 hours, followed by addition of NaOH (20 mL, 2 M) until basic conditions. The reaction mixture was extracted with ethyl acetate (3*50 mL) and the combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M), and the organic phases were dried (MgSO4) and evaporated to dryness to produce 0.69 g of crude 19. The crude product was subjected to CC [eluent: CH2Cl2: MeOH (99:1)] to give pure 19 (0.40 g, 64%); LC-MS [M+H]+315 (cald. 315.5).

The synthetic route of 31599-60-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Acadia Pharmaceuticals Inc.; US6528529; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 355-43-1, The chemical industry reduces the impact on the environment during synthesis 355-43-1, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane, I believe this compound will play a more active role in future production and life.

In a typical procedure compound 2 (50.0 g, 0.147 mol), 10% aqueous solution of Na2S2O5 (140 mL) and perfluoro hexyl iodide (67.0 g, 0.150 mol) was added into a 1.0 L flask and the mixture heated at 80 C under stirring. AIBN (1.0 g, 6.1 mol) was slowly added (four portions of 0.2 g each in 1 h). It was left to react at 80 C for 3 h under stirring. At the end the organic phase containing 110.9 g (0.14 mol, Y = 96%) of 5 was separated from the aqueous one and washed with water. Compound 5 (20.0 g, 0.025 mol) was charged in the autoclave and a solution containing 70 mL ethylacetate, 50 mL methanol, and 7 g of sodium acetate was added; 1.0 g of Pd/C (10%) suspended in 20 mL of methanol was charged. The mixture was left to react at room temperature at a pressure of 3 bar of hydrogen for 15 h. The raw mixture was filtered and solvents were removed with rotary evaporation. Successively 100 mL of water and 100 mL of Et2O were added to the solid residue. The organic phase was dried with magnesium sulphate and the solvent layer was eliminated under rotary evaporation. The crude material was distilled under vacuum in order to obtain 13.5 g (0.020 mol) of product 8 with a yield of 82%.

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, 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lazzari, Dario; Cassani, Maria Cristina; Solinas, Gavino; Pretto, Marisa; Journal of Fluorine Chemistry; vol. 156; (2013); p. 34 – 37;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 35944-64-0, name is 3-Iodo-4-methylaniline, 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 35944-64-0, name: 3-Iodo-4-methylaniline

N-(3-Iodo-4-methylphenyl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trfluoromethy1)benzamide: To a flask containing 1,0 g (2.67 mmol) of 4-[(4-methyl-1- piperazinyl)rnethyl]-3 -(trifluoromethyl)-benzoic acid (CAS 859027-02-4; prepared according toAsaki, T. et al. Bioorg. Med. Chem. Lelt. (2006), 16, 1421-1425), 0.62 g (2.67 mmol) of 3-lodo-4-methylanil me, 0.77 g (4.0 mmol) of N-(3 -dimethylaminopropyl)-N?-ethylcarbodi imide hydrochloride (EDAC), and 0.43 g (3.2 mmol) of N-hydroxybenzotriazole monohydrate (HOBt H20) was added 5 mL of DCM and 5 mL of triethylamine. The solution was stirred at ambient temperature under an atmosphere of N2 for 3 days, concentrated, and the crude product purified by silica gel chromatography (eluted with 100% EtOAc then 10% MeOH/EtOAc), to provide0.69 g of product as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodo-4-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; GOZGIT, Joseph, M.; RIVERA, Victor, M.; SHAKESPEARE, William, C.; ZHU, Xiaotian; DALGARNO, David, C.; WO2013/162727; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com