Tag: M.W=200-300

77317-55-6, These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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.

General procedure: CuCl (1.50 mg, 0.0150 mmol), DPEPhos (8.10 mg, 0.0150 mmol) and KOt-Bu (1.70 mg,0.0150 mmol) were added to a 8 mL vial charged with a magnetic bar. The vial was sealedwith a cap (phenolic open top cap with gray PTFE/silicone) and purged by N2 gas for 5 min.Toluene (0.8 mL) and methyl 2-aminobenzoate (1a) (46.6 L, 0.360 mmol) were added to themixture, which was allowed for 10 min. And then a solution of phenyl vinyl sulfone (2) (50.5mg, 0.300 mmol) in toluene (0.7 mL) was added to the reaction solution. After stirring atroom temperature for 5 h, THF (5 mL) was added and the reaction was allowed to cool to 0C (ice bath). After addition of KOt-Bu (101 mg, 0.900 mmol), the resulting solution wasallowed to stir for further 1 h at 0 C. After that time, the reaction was quenched with asaturated aqueous solution of NH4Cl (1 mL) and NaHCO3 (2 mL) and washed with EtOAc (7x 3 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated invacuo. The crude product was purified by silica gel column chromatography (CH2Cl2/EtOAc,8:1) to afford the desired product 4a (76.8 mg, 0.267 mmol, 89% yield) as a yellow solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 77317-55-6.

Reference:
Article; Kang, Seongil; Yoon, Hongju; Lee, Yunmi; Chemistry Letters; vol. 45; 12; (2016); p. 1356 – 1358;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 116632-39-4, name is 5-Bromo-2-iodotoluene, I believe this compound will play a more active role in future production and life. 116632-39-4

Ethyl 4-pyrazolecarboxylate (202 mg, 1.44 mmol), 5-bromo-2-iodotoluene (0.20 mL, 1.4 mmol), (15,25,N7E,N2i^-N7,N2-bis(pyridin-2-ylmethylene)cyclohexane-l,2-diamine (84 mg, 0.29 mmol), Copper(I) oxide (10 mg, 0.072 mmol), and cesium carbonate (939 mg, 2.88 mmol) were combined in a 5 mL microwave vial and dissolved in acetonitrile (3.0 mL). The reaction was stirred at 82C overnight. The reaction was then filtered through Celite rinsing with ethyl acetate. The solution was concentrated in vacuo and purified by silica chromatography, eluting with 10-25% ethyl acetate in hexanes to give ethyl l-(4-bromo-2-methylphenyl)-lH- pyrazole-4-carboxylate.LRMS (ESI) calc’d for Ci3Hi4BrN202 [M+H]+: 309, found 309.

The chemical industry reduces the impact on the environment during synthesis 116632-39-4. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 612-55-5, name is 2-Iodonaphthalene, molecular formula is C10H7I, 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. 612-55-5

General procedure: An aryl iodide (2′: 0.20 mmol) in a 20 mL Schlenk tube was added successively toluene (1.5 mL), a THF solution of an arylmagnesium bromide (1: 0.30 mmol) and THF (overall 0.50 mL), and the resulting mixture was stirred at 80 C for 24 h. After cooling, the reaction mixture was quenched with a 1 N HCl aqueous solution (1.0 mL) and extracted with Et2O (10 mL x 3). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was subjected to silica gel chromatography (hexane orhexane/diethyl ether, PTLC) to give the corresponding coupling product (3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 612-55-5, its application will become more common.

Reference:
Article; Shirakawa, Eiji; Okura, Keisho; Uchiyama, Nanase; Murakami, Takuya; Hayashi, Tamio; Chemistry Letters; vol. 43; 6; (2014); p. 922 – 924;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

55406-53-6, A common heterocyclic compound, 55406-53-6, name is 3-Iodoprop-2-yn-1-yl butylcarbamate, molecular formula is C8H12INO2, 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.

EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of IPBC was determined by means of HPLC at the beginning and after two weeks.

The synthetic route of 55406-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Uhr, Hermann; US2009/36555; (2009); 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. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., 3032-81-3

A 1000-mL flask equipped with overhead stirrer, condenser and thermometer was charged with l,3-dichloro-5-iodobenzene (99.0 g, 0.36 mol), 1,3-dimethyl 2-(3,5- dichlorophenyl)propanedioate (91.0 g, 0.69 mol), copper(I) iodide (4.0 g, 0.021mol), 2-picolinic acid (5.2 g, 0.042 mol) and cesium carbonate (350 g, 1.07 mol) in 1,4-dioxane (600 mL). The reaction mixture was heated under nitrogen to 90 C for 3 hours. The mixture was then cooled to 30 C, diluted with water (300 mL) and hexane (200 mL), and partitioned. The organic phase was washed with saturated aqueous ammonium chloride solution (200 mL) and concentrated under vacuum to a viscous oil. The resulting material was used directly in the next step.

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Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; HOFFMANN, Christian; ZHANG, Wenming; CHEN, Yuzhong; WO2013/192035; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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.

Under N2, a suspension of methyl 2-amino-5-iodobenzoate (4) (2.77 g, 10 mmol), Pd(PPh3)4 (1.159 mg, 1 mmol), CuI (381 mg, 2 mmol), Et3N (4.2 mL, 30 mmol) and propargyl alcohol (1.75 ml, 30 mmol) in DMF (20 mL) was stirred at rt for 15 h. TLC analysis (petrol ether: ethyl acetate 1:1) indicated the fully consumption of starting material. The reaction was quenched with 200 ml sat. NaCl solution. Ethyl acetate: petrol ether 1:1 (200 ml) was added to the mixture and the aqueous layer was extracted with ethyl acetate:petrol ether 1:1 three times. After drying the combined organics over MgSO4, the solution was concentrated and purified by silica gel chromatography (petrol ether:ethyl acetate 80:20 to ethyl acetate), giving Compound 5 as a yellow oil (1.88 g, 92%). 1H NMR (CDCl3) delta 3.78 (s, 3H), 4.25 (s, 2H, CCH?2), 7.27-7.36 (m, 2H, arom.H), 7.58-7.65 (m, 1H, arom.H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 77317-55-6.

Reference:
Patent; Illumina, Inc.; Illumina Cambridge Limited; Wu, Xiaolin; Smith, Randall; Shieh, Peyton; Beierle, John M.; George, Wayne N.; Lawrence, Elliot John; Mao, Jie; Liu, Xiaohai; (62 pag.)US2019/352327; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 660-49-1, name is 3-Fluoro-5-iodoaniline, molecular formula is C6H5FIN, 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. 660-49-1.

Production Example 342 benzhydrylidene-(3-fluoro-5-iodophenyl)-amine 0.75 g of the title compound (yellow oil) was obtained from 3.2 g of 3-fluoro-5-iodophenylamine (compound in Production Example 341) by the same reaction as in Production Example 336.1H-NMR (CDCl3) delta: 6.36-6.43(m, 1H), 6.86-6.92(m, 1H), 6.96-7.02(m, 1H), 7.08-7.16(m, 2H), 7.28-7.54(m, 6H), 7.68-7.76(m, 2H)

The synthetic route of 3-Fluoro-5-iodoaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; EP1382603; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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.

General procedure: To a solution of NCTD (1, 1.0 g, 5.95 mmol) dissolved in tetrahydrofuran (THF, 10 mL)accompanied by triethylamine (TEA, 0.5 mL) as the acid-binding agent was added the correspondingaromatic amine (1 equiv., 5.95 mmol). When the reaction was complete after 14 h as checkedby TLC analysis, the solution was concentrated under reduced pressure and diluted with acetone(100 mL). The resulting filter cake was either recrystallized from methanol or purified by columnchromatography (MeOH/CH2Cl2, 1: 4, v/v) to afford the desired products II (1-36). The yields,physical properties, 1H-NMR, 13C-NMR, and HRMS-ESI of the target compounds II were as follows.

The synthetic route of 13194-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yang; Sun, Wenbo; Zha, Shunqing; Wang, Huan; Zhang, Yalin; McPhee, Derek J.; Molecules; vol. 20; 12; (2015); p. 21464 – 21480;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 64248-58-4

General procedure: General procedure for the synthesis of alpha-arylacetic acid tert-butyl esters: A Schlenk tube was charged with aryl iodide (1.0mmol), CuI (9.5mg, 0.05mmol), 2-picolinic acid (12mg, 0.10mmol), and cesium carbonate (978mg, 3.0mmol). The tube was evacuated and backfilled with argon three times before tert-butyl acetoacetate (2.0mmol) and 2mL of 1,4-dioxane was added. The tube was immersed in an oil bath, and the reaction mixture was stirred at the indicated temperatures for 33-48h. The cooled mixture was partitioned between ethyl acetate and saturated NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with PE/EA=20:1 to 3:1) to provide the desired alpha-arylacetic acid tert-butyl esters.

The synthetic route of 64248-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Conference Paper; Zhao, Duo; Jiang, Yongwen; Ma, Dawei; Tetrahedron; vol. 70; 20; (2014); p. 3327 – 3332;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 452-68-6, name is 1-Fluoro-4-iodo-2-methylbenzene, 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. 452-68-6

To a dry 25 ml flask fitted with nitrogeninlet/outlet was addedK3PO4 (0.589 g), ethylene glycol (0.178 g), 2-fluoro-5-iodotoluene (0.368 g), copper(l) iodide (0.028 g) and Example28 (0.516 g). To this was added previously degassed anhydrous propan-2-ol (10ml). This was then subjected to a nitrogen/vacuum cycle. The reaction was then heated to reflux for 17.5 hours under a nitrogen atmosphere. After this time the reaction was filtered, and the liquors poured into water (50ml). This was then extracted with DCM (1 x 30 ml and 2 x 20ml), the organic layers combined and washed with 1 M ammonia solution (1 x 100 ml) then 1M ammonia solution (1 x 50ml) and water (1 x 50ml). The organics were dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was thencolumned over silica (30 g) using DCM/EtOAc as eluent. This afforded 0.140 g of the title compound.8H (DMSO-d6) 8.74(1H, s), 7.78-7. 75 (1H, d, J 9.7 Hz), 7.65- 7.61 (3H, m), 7.58-7. 51 (2H, m), 7.02-6. 96 (1H, t), 6.82-6. 79 (1H, m), 6.76- 6.72 (1 H, m), 6.53-6. 49 (1 H, d, J 9.7 Hz), 4.63-4. 60 (1 H, t), 3.89 (1 H, broad), 3.28-3. 21 (3H, m), 2.80-2. 78 (1H, m), 2.14 (3H, s), 1.71-1. 51 (4H, m). LCMS ES+ RT 3.29 min, 478.0 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 452-68-6.

Reference:
Patent; CELLTECH R & D LIMITED; WO2004/113349; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com