Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 2265-91-0, name is 1,3-Difluoro-5-iodobenzene, 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 2265-91-0, Product Details of 2265-91-0

General procedure: o-hydroxy-cinnamate ester 1 (0.5 mmol,), aryl iodides 2 (1.0 mmol, 2.0 equiv), Pd(OAc)2 (0.05 mmol, 10 mol %), and H2O (1ml) was charged into a pressure tube. The reaction mixture was stirred at 100 C for 12 h under air. After cooled to room temperature, the reaction mixture was diluted with EtOAc (5 mL) and washed with NH4Cl (3 x 5 mL). The organic phase was separated, dried over NaSO4 and the solvent was removed in vacuo. The residue was purified by column chromatography by using hexanes/ethyl acetate as eluent to afford the desired products 3a-z.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Difluoro-5-iodobenzene, and friends who are interested can also refer to it.

Reference:
Article; Chen, Junmin; Liu, Wei; Zhou, Liandi; Zhao, Yongli; Tetrahedron Letters; vol. 59; 26; (2018); p. 2526 – 2531;,
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. 40400-15-5, name is 2-(2-Iodophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Safety of 2-(2-Iodophenyl)acetonitrile

General procedure: General procedure for indole synthesis by Cu-catalyzed amidation reaction. A dried re-sealable vialwith a Teflon stir bar was charged with amide (3.0 equiv, 1.5 mmol), CuI (5 mol%, 0.025 mmol), K3PO4(2.0 equiv, 1.0 mmol). The vial was sealed with a rubber septum and evacuated and refilled with argonthree times through a syringe needle. Under an argon atmosphere, toluene (0.5 mL),trans-1,2-diaminocyclohexane (20 mol%, 0.1 mmol) and aryl halide (0.50 mmol) were each added viasyringe. The rubber septum was then removed and quickly replaced with a Teflon screw cap and thereaction mixture was stirred at 110 C for 24 h. The resulting suspension was allowed to reach roomtemperature and filtered through a pad of silica gel eluting with AcOEt (10 mL). The filtrate wasconcentrated and the residue was purified by flash chromatography to afford a pure product.

The synthetic route of 40400-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abe, Masahiro; Denneval, Charline; Nozawa-Kumada, Kanako; Kondo, Yoshinori; Heterocycles; vol. 92; 5; (2016); p. 900 – 909;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 1133123-02-0,Some common heterocyclic compound, 1133123-02-0, name is 4-Bromo-2-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.

To a stirred solution of 4-bromo2-iodobenzoic acid 319a (3 0 g, 1 equiv.) in THF (405 mL) was added di-tert-butyl dicarbonate (3.0 g, 1.5 equiv.), TEA (3.2 mL, 2.5 equiv.) andDMAP (1. 1 g, 1.0 equiv.). The reaction mixture was stirred at room ternperature for 16 h,diluted with ethyl acetate, and washed with water, brine, dried over sodium sulfate, filteredand concentrated under reduced pressure. The residue was purified by silica gelchromatography eluting with 3-5~o ethyl acetate in hexanes to give the tert-bu1yl4-bromo-2-10 iodobenzoate 319b (1.9 g) as a liquid. 1HNMR (400 MHz, DMSO-d6) 8: 8. J 8 (d, l”l.9 Hz,1H), 7.76-7.60 (m lH), 7.54 (d, J = 8.3 Hz, lH), 156 (bs, 9H).

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

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 14452-30-3, A common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, molecular formula is C8H7IO, 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 cooled (-40 C) stirred solution of TiCH (11 mL of a 1.0 M sol in DCM, 11 mmol) in 5 mL of DCM was added dimethyl zinc (5.5 mL of a 2 N sol. in toluene, 11 mmol). After stirring for 10 min iodoacetophenone (1. 23 g, 5.0 mmol) was added. After 2 h the reaction was warmed to 0 C and stirred for an additional 1 h. The reaction was poured onto ice and extracted with ether. The organic phase was washed with water and sat NaHCO3. The organic phase was dried over magnesium sulfate, filtered, and dried under reduced pressure. The material was distilled using a kugelrohr (80 C at 0.1 mm) to obtain 1.0 g (76% yield) of a clear oil. 1-tert-Butyl-3-iodo-benzene. To a cooled (-40 C) stirred solution of TiCH (11 mL of a 1.0 M sol in DCM, 11 mmol) in 5 mL of DCM was added dimethyl zinc (5. 5 mL of a 2 N sol. in toluene, 11 mmol). After stirring for 10 min lodoacetophenone (1. 23 g, 5.0 mmol) was added. After 2 h the reaction was warmed to 0 C and stirred for an addtional 1 h. The reaction was poured onto ice and extracted with ether. The organic phase was washed with water and sat NaHCO3. The organic phase was dried over magnesium sulfate, filtered, and dried under reduced pressure. The material was distilled using a kugelrohr (80 C at 0.1 mm) to obtain 1.0 g (76% yield) of a clear oil ; 1H NMR (300 MHz, CDCI3) 5 7.71 (t, J = 2.0 Hz, 1 H), 7.51 (dt, J = 7.7, 1.3 Hz, 1 H), 7.35 (app d, J = 7.7 Hz, 1 H), 7.03 (t, J= 7. 9 Hz, 1 H), 1.29 (s, 9H).

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; ELAN PHARMACEUTICALS, INC.; WO2005/70407; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 755027-21-5, The chemical industry reduces the impact on the environment during synthesis 755027-21-5, name is 4-Chloro-1-iodo-2-methoxybenzene, I believe this compound will play a more active role in future production and life.

A mixture of Example 56A (67mg, 0.2 MMOL), Example 59B (37mg, 0.2 mmol), CYMAP ligand (11. 8mg, 0.03 mmol), Pd (OAc) 2 (4.9mg, 0.002 mmol), and CsF (91MG, 0.6 mmol) in DME (8 mL) and methanol (4 mL) was heated to reflux overnight, cooled to room temperature, and partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (MGS04), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 1: 1 HEXANES/ETHYL acetate to provide 0.036g (50%) of the desired product. MS (ESI) m/e 359 (M+H) + ; 1H NMR (300 MHz, DMSO-d6) 8 9.88 (s, 1H), 7.99 (s, 1H), 7.79 (d, J = 8.14 Hz, 1H), 7.70 (d, J = 8.14 Hz, 1H), 7.27-7. 36 (m, 3H), 6.91-7. 01 (m, 5H), 4.00 (s, 3H), 2.56 (s, 3H).

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

Reference:
Patent; ABBOTT LABORATORIES; WO2004/76424; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 481075-58-5,Some common heterocyclic compound, 481075-58-5, name is 2-Bromo-1-iodo-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF3I, 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.

General procedure: 2-aminobenzenethiol (10 g, 80mmol), 3, 4-difluorobenzonitrile (11.12, 80mmol) and ferric citrate (19.59g, 80mmol) were added in DMF (50.00 mL) at 25-30 0C. The reaction mixture was heated to 110C. Reaction mixture was monitored for the synthesis of compound 3 by TLC. (2ml of reaction mixture was withdrawn and separated in ethylacetate and water. Ethyl acetate solution concentrated and crystallised in isopropyl ether to give compound 3 for characterization). After completion of reaction by TLC, powdered potassium carbonate (16.58 g, 120mmol) was added to the solution and stirred for 1 hr. The mixture was heated to 110C till completion by TLC. After completion of reaction, the mass was cooled to 25-30 C. Ethyl acetate (150 mL) and DM water (150 mL) were added. Layers separated. Organic layer washed with water (150 mL), dried over sodium sulfate and concentrated. Isopropyl ether (IPE; 150 mL) was added to the slurry, filtered, washed with IPE. Dried under vacuum at 50 C (16.84g, 94%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-iodo-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Article; Das, Tonmoy Chitta; Quadri, Syed Aziz Imam; Farooqui, Mazahar; Letters in Organic Chemistry; vol. 16; 1; (2019); p. 16 – 24;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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. SDS of cas: 624-75-9

The compound obtained in Example 64 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and the residue was treated in water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of regioisomers as yellow oil. These two regioisomers (4.16 g, 80%) were used in the next reaction step without separation.Example 65-2Preparation of 4-(2-chloropyridin-5-yl)-5-(3-methoxy-5-methylphenyl)-pyrazol-1-yl)acetonitrile1H NMR (CDCl3) delta 2.28 (s, 3H), 3.66 (s, 3H), 5.16 (s, 2H), 6.71 (s, 2H), 6.84 (s, 1H), 7.24 (d, J=8.3 Hz, 1H), 7.49 (dd, J=2.3, 5.9 Hz, 1H), 7.70 (s, 1H, 8.32 (s, 1H); 13C NMR (CDCl3) delta 21.57, 39.89, 55.23, 110.80, 113.76, 115.28, 117.76, 121.47, 124.02, 127.24, 129.92, 132.57, 138.58, 140.12, 148.71, 149.92, 151.17, 159.69, 162.33.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 65 (0.32 g, 0.95 mmol), 3-acetylphenylboronic acid (0.19 g, 1.13 mmol), dichlorobis(triphenylphosphine)palladium (II) (33 mg, 0.04 mmol) and potassium carbonate (0.13 g, 0.95 mmol). The reaction system was purged with nitrogen gas for 10 min, and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled at room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:2, v/v): (106 mg); m.p. 149-150 C.; 1H NMR (CDCl3) delta 2.37 (s, 3H), 2.67 (s, 3H), 3.78 (s, 3H), 4.95 (s, 2H), 6.71 (s, 1H), 6.77 (s, 1H), 6.87 (s, 1H), 7.51-7.70 (m, 3H), 7.92 (s, 1H), 7.97 (d, J=7.6 Hz, 1H), 8.16 (d, J=7.8 Hz, 1H), 8.53 (s, 1H), 8.57 (d, J=1.2 Hz, 1H); 13C NMR (CDCl3) delta 21.61, 26.82, 37.80, 55.41, 112.41, 114.22, 116.66, 118.39, 120.33, 122.71, 126.53, 126.96, 128.67, 129.04, 129.09, 131.18, 135.01, 137.58, 139.36, 139.48, 141.15, 141.36, 147.96, 154.21, 160.37, 198.06.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 624-75-9, its application will become more common.

Reference:
Patent; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
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. 101066-87-9, name is 4-Iodo-2-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 101066-87-9

General procedure: Under N2 atmosphere, a mixture of intermediate 12 (263.5 mg,1.0 mmol), 3-bromoaniline (172.0 mg, 1.0 mmol), Cs2CO3 (325.8 mg,1.0 mmol), Pd2(dba)3 (45.8 mg, 0.05 mmol) and Davephos (31.5 mg,0.08 mmol) in MeCN (6.0 ml) was heated to reflux for 5 h. The reactionmixture was cooled to room temperature and diluted withethyl acetate. The resulting mixturewas filtered off and the solutionwas concentrated under vacuum to give a crude product 16 thatwas purified by column chromatography on silica using a solvent of10% ethyl acetate in hexanes. The desired compound 16 was obtainedas a yellow solid (220.0 mg, yield 72%). For the synthesis ofintermediate 13-15, compound 12 or commercially available 11and corresponding aromatic amine were used respectivelyfollowing the procedure described for 16.

According to the analysis of related databases, 101066-87-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yu, Jiang; Zhang, Lanxi; Yan, Guoyi; Zhou, Peiting; Cao, Chaoguo; Zhou, Fei; Li, Xinghai; Chen, Yuanwei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 265 – 281;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 41252-95-3, The chemical industry reduces the impact on the environment during synthesis 41252-95-3, name is 1-Chloro-4-iodo-2-nitrobenzene, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of the aryl iodide (1.0 mmol), 10% Pd/C (0.05 mmol), PPh3 (0.20 mmol), and K2CO3 (2.0 mmol) was stirred in H2O (5 mL) at room temperature under an argon atmosphere. 2-Imino-1-(2-propynyl)pyrimidine (2) (1.20 mmol) was added, and the mixture was stirred at 95 C for 10 h. After completion of the reaction, the resulting solution was concentrated in vacuo, and the crude product was subjected to column chromatography (silica gel) using CHCl3-CH3OH (98:2) as eluent to afford the pure product.

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-Chloro-4-iodo-2-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bakherad, Mohammad; Keivanloo, Ali; Kalantar, Zahra; Jajarmi, Saeideh; Tetrahedron Letters; vol. 52; 2; (2011); p. 228 – 230;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 52570-33-9,Some common heterocyclic compound, 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, 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.

Under a nitrogen atmosphere, 2-amino-3-bromo-5- methylpyridine (2.00 g, 10.69 mmol) , methyl 3-iodo-2- methylbenzoate (2.95 g, 10.69 mmol) , copper (I) iodide (204 mg, 0.11 mmol), ethanol amine (131 mg, 0.22 mmol), potassium carbonate (2.22 g, 16.04 mmol), and anisole (30 ml) were mixed, and the mixture was stirred at room temperature for 10 minutes. The mixture was heated and stirred at 130C for 8 hours. The reaction solution was cooled to room temperature, and water (30 ml) was added thereto. The mixture was concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate (50 ml), activated carbon Shirasagi A was added, and the mixture was filtered. Water (20 ml) was added to the filtrate. The organic layer was separated and washed with water (20 ml) . The organic layer was concentrated. The concentrate was subjected to silica gel column chromatography (silica gel 20 g, eluent: ethyl acetate :n-hexane = 1:20), and the effective fraction was concentrated. Ethyl acetate (0.2 ml) and n-hexane (5 ml) were added to the residue, and the mixture was stirred at room temperature for 30 minutes. Next, the crystals were collected by filtration, and dried at 50C under reduced pressure, to yield the title compound (1.13 g) . (HPLC area%: 83.4% (methyl 3- [ (3-iodo-5-methylpyridin-2- yl) amino] -2-methylbenzoate: 16.1%)) .

The synthetic route of 52570-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/16184; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com