Category: iodides-buliding-blocks

Application of 40400-15-5, A common heterocyclic compound, 40400-15-5, name is 2-(2-Iodophenyl)acetonitrile, molecular formula is C8H6IN, 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.

A solution of 2-(2-iodophenyl)acetonitrile (1.00 g, 4.1 1 mmol) in anhydrous THF (5 mL) under an atmosphere of nitrogen was treated with borane tetrahydrofuran complex solution (1.0 M in THF, 12.3 mL, 12.3 mmol). The mixture was stirred at reflux for 16 h, cooled to room temperature and excess borane reagent was quenched by the dropwise addition of water (until evolution of hydrogen ceased). MeOH (2.5 mL) and cone. H2S04 (0.5 mL) was added and the mixture was stirred for 1 h at r.t.. The mixture was concentrated in vacuo, water (-10 mL) was added and the aqueous was adjusted to pH -12 with aq. NaOH (2 M). The aqueous layer was extracted with EtOAc (3 * 30 mL), the organics were combined, washed with brine, dried (Na2S04) and the solvent removed in vacuo to give a colourless oil. Water (-20 mL) was added and the aqueous phase was adjusted to pH ~2 with aq. HCI (2 M). The aqueous layer was washed with DCM (3 chi 30 mL) and then adjusted to pH -12 with aq. NaOH (2 M). The aqueous layer was extracted with DCM (3 x 50 mL), the organics were combined, washed with brine, dried (Na2S04) and the solvent removed in vacuo to give the product as a colourless oil (0.869 g, 85% yield): 1H NMR (400 MHz, DMSO-d6) delta 7.81 (dd, J = 7.8, 1.2 Hz, 1H), 7.35 – 7.27 (m, 2H), 6.97 – 6.91 (m, 1H), 2.75 – 2.71 (m, 4H) exchangeable NH not observed; LCMS-B RT 2.77 min; m/z 248.0 [M+H]+.

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

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
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148870-57-9, name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one

A mixture of the iodo-compound of formula (III) (50.00 g; 129 mmol), amine hydrochloride of formula (IV) (31.50 g; 129 mmol), potassium carbonate (37.70 g; 273 mmol), toluene (80 ml) and water (40 ml) was heated to 70C with stirring under an argon atmosphere. Reaction progress was monitored by HPLC. Upon completion, the reaction mixture was cooled to 23 C, diluted with toluene (105 ml), and filtered through a pad of celite. The filter cake was washed with additional toluene (60 ml). To the filtrate, water (50 ml) was added, and the mixture was shaken. The organic layer was separated and washed with additional water (80 ml). The separated organic layer was then extracted with 9% aqueous hydrochloric acid (507 g) in three portions. Yield of dehydroivabradine hydrochloride in combined acidic extracts was calculated based on HPLC assay using an external standard. The product was obtained in 80% yield as an aqueous solution which was used directly in the next step.

The synthetic route of 148870-57-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNTHON BV; MEL?A, Petr; ZABADAL, Miroslav; WO2014/114341; (2014); A1;,
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Application 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.

1-Bromo-4-iodo-2-methoxybenzene (50 g, 160 mmol) was suspended in dichloromethane (75 mL) at -10 C. Boron tribromide (250 mL, 250 mmol, 1M in CH2Cl2,) was cannulated in over 30 minutes, with the internal temperature remaining below 0 C throughout the addition. After the addition, the mixture was stirred at 0 C for 1 h, and then at room temperature for 16 h. The mixture was cooled in an ice bath and 10% aqueous Na2CO3 (250 mL) was added in portions. The mixture was then partitioned between H2O and dichloromethane. The dichloromethane layer was dried over MgSO4 and then filtered.2-Bromo-5-iodophenol (46 g, 96%) was obtained from the filtrate as a pinkish-white solid. 1H NMR (acetone-d6) d: 9.24 (br s, 1H), 7.38 (d, J= 2 Hz, 1H), 7.31 (d, J= 8.5 Hz, 1H), 7.17 (dd, J= 8.5 Hz, 2 Hz, 1H).

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; PTC THERAPEUTICS, INC.; ZHANG, Nanjing; BABU, Suresh; BARRAZA, Scott J.; BHATTACHARYYA, Anuradha; CHEN, Guangming; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; SYDORENKO, Nadiya; TURPOFF, Anthony; WOLL, Matthew, G.; YAN, Wuming; (0 pag.)WO2020/5877; (2020); 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. 19230-28-5, name is 1,3-Dichloro-2-iodobenzene, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

A mixture of7-chloro-2-(trimethylstannyl)furo[2,3-c]pyridine (63 mg, 0.23 mmol), 1,3-dichloro-2-iodobenzene (73 mg, 0.27 mmol), Pd2(dba)3(10 mg, 0.011 mmol), tris(2-furyl)phosphine (5 mg, 0.022 mmol) and NMP (2 mL)was degassed with N2for 10 min. The resulting mixture was irradiated in a microwave reactor at 130 C for 0.5 h. The mixture was allowed to cool to room temperature, poured into water (25 mL) and extracted with diethyl ether (2 x 50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated. The residue was purified by silica gel column chromatography eluting with a 0-100% gradient of diethyl ether in heptane. Appropriate fractions were combined and evaporated to afford the title compound (49 mg, 83% yield) as a white solid. H NMR (400 MHz, DMSO-d6): delta 8.31 (1H, d,J= 5.3 Hz), 7.87 (1H, d,J= 5.1 Hz), 7.76 – 7.72 (2H, m), 7.69 – 7.65 (1H, m), 7.50 (1H, s); LCMS (ESI) m/z: 298.2 [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:
Article; Liang, Jun; Van Abbema, Anne; Balazs, Mercedesz; Barrett, Kathy; Berezhkovsky, Leo; Blair, Wade S.; Chang, Christine; Delarosa, Donnie; DeVoss, Jason; Driscoll, Jim; Eigenbrot, Charles; Goodacre, Simon; Ghilardi, Nico; MacLeod, Calum; Johnson, Adam; Bir Kohli, Pawan; Lai, Yingjie; Lin, Zhonghua; Mantik, Priscilla; Menghrajani, Kapil; Nguyen, Hieu; Peng, Ivan; Sambrone, Amy; Shia, Steven; Smith, Jan; Sohn, Sue; Tsui, Vickie; Ultsch, Mark; Williams, Karen; Wu, Lawren C.; Yang, Wenqian; Zhang, Birong; Magnuson, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4370 – 4376;,
Iodide – Wikipedia,
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Electric Literature of 5458-84-4, These common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, 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.

A mixture of 1-iodo-2-methoxy-4-nitrobenzene (2.0 g, 7.16 mmol), methyl acrylate (2.0 mL, 22.2 mmol), Pd(OAc)2 (100 mg) and PPh3 (200 mg) in DMF (20 mL) was purged with argon and heated to 70 C overnight. TLC showed that the starting material was consumed completely and a new spot had formed. The reaction mixture was diluted with ethyl acetate and the catalyst was removed by filtration. The organic layer was washed with brine, dried over Na2504 and concentrated under reduced pressure. The residue was purified by silica gel column (petroleum ether 100%) to give methyl (E)-3-(2-methoxy-4-nitrophenyl)acrylate as a yellow solid (500 mg, 31%).?H NMR (400 MHz, CDC13): 7.96 (d, J = 16.0 Hz, 1H), 7.84 (dd, J = 8.4 Hz, 2.0 Hz, 1H), 7.77 (d, J = 2.0 Hz, 1H), 7.63 (d, J = 8.4 Hz, 1H), 6.63 (d, J = 16.4 Hz,1H), 4.00 (s, 3H), 3.83 (s, 3H).

The synthetic route of 5458-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVOGEN LIMITED; EIFFE, Eleanor; HEATON, Andrew; GUNNING, Peter; TREUTLEIN, Herbert; ZENG, Jun; JAMES, Ian; DIXON, Ian; (172 pag.)WO2016/187667; (2016); 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. 886762-68-1, name is 1,3-Difluoro-5-iodo-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1,3-Difluoro-5-iodo-2-methoxybenzene

Example 12i 5-(3-Bromo-4-fluorophenyl)-5-(3,5-difluoro-4-methoxyphenyl)-5H-pyrrolo[3,4-b]pyridin-7-amine tert-Butyllithium (0.995 mL, 1.59 mmol) was added dropwise to THF (4 mL) at -100 C. under an argon atmosphere. A solution of 1,3-difluoro-5-iodo-2-methoxybenzene (215 mg, 0.80 mmol) in THF (1 mL) was added dropwise followed by the addition of N-((3-bromo-4-fluorophenyl)(2-cyanopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide (250 mg, 0.61 mmol) in THF (2 mL). The resulting reaction mixture was left on the thawing cooling bath for 30 min then the cooling bath was removed and the mixture was stirred at r.t. for 1 h. Hydrogen chloride in methanol (3 mL, 3.7 mmol) was added and the resulting mixture was stirred at r.t. for 1 h. The mixture was concentrated and purified on a silica gel column eluted with 0-10% NH3 (0.1 M in MeOH) in DCM. This gave 52 mg (19% yield) of the title product: MS (ES) m/z 448, 450 [M+1]+.

According to the analysis of related databases, 886762-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2010/125081; (2010); A1;,
Iodide – Wikipedia,
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Application of 153898-63-6,Some common heterocyclic compound, 153898-63-6, name is 2-Iodo-5-methoxyaniline, molecular formula is C7H8INO, 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.

NaBH(OAc)3 (5.10 g, 24.1 mmol) was added to a solution of p-anisaldehyde (0.41 mL, 6.63 mmol), 2-iodo-5-methoxyaniline5 (1.5 g, 6.02 mmol) and AcOH (0.11 mL, 0.11 mmol) in 1,2-DCE (30 mL). The mixture was stirred 24 h, then saturated aq. KHCO3 (15 mL) was slowly added while stirring vigorously. The aqueous layer was extracted with EtOAc, the combined organic layer was washed with brine, dried over MgSO4, and volatile compounds were removed under vacuum. The residue was subjected to flash chromatography (20% EtOAc in hexanes) to give the title compound (1.80 g, 81%). 1H NMR (400 MHz, CDCl3) delta 7.50 (d, J = 8.6 Hz, 1H), 7.26 (d, J= 8.6 Hz, 2H), 6.87 (d, J= 8.6 Hz, 2H), 6.14 (d, J = 2.8 Hz, 1H), 6.07 (dd, J = 8.6 Hz, 2.8 Hz, 1H), 4.49 (s, 1H), 4.27 (s, 1H), 4.26 (s, 1H), 3.78 (s, 3H), 3.69 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 161.2, 158.8, 147.9, 138.9, 130.3, 128.5, 114.0, 104.0, 97.9, 74.5, 55.2, 47.8

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodo-5-methoxyaniline, its application will become more common.

Reference:
Article; Zhang, Hanmo; Hay, E. Ben; Geib, Stephen J.; Curran, Dennis P.; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1649 – 1655;,
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. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, A new synthetic method of this compound is introduced below., Computed Properties of C6H3Cl2I

General procedure: Amide derivatives (0.2 mmol), 4-methoxy iodobenzene (3 equiv.), Pd(OAc)2 (10 mmolpercent), C6H13COOAg (2 equiv.) were combined in o-xylene (1 mL) in a 10mL vial. The vial was sealed with a Teflon lined cap, and the reaction was stirred in 120 ¡ãC oil bath for 24 hours without an inert gas atmosphere. After cooled to room temperature, the mixture was extracted with ethyl acetate (3 x 10mL). The residue was purified by silica-gel column chromatography to afford the corresponding product.

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; Yan, Xufei; Long, Rongrong; Luo, Feihua; Yang, Li; Zhou, Xiangge; Tetrahedron Letters; vol. 58; 1; (2017); p. 54 – 58;,
Iodide – Wikipedia,
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Related Products of 4387-36-4,Some common heterocyclic compound, 4387-36-4, name is 2-Iodobenzonitrile, molecular formula is C7H4IN, 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.

Weigh 2.28 g of o-iodobenzonitrile and 1.13 g of phenylacetylene. Bis-triphenylphosphine palladium dichloride 140mg, 19 mg of cuprous iodide is dissolved in 250 mL of triethylamine. The reaction was carried out under nitrogen at 60 C for 12 h. Thin chromatography was used to detect the reaction process. After the reaction is completed, it is filtered with diatomaceous earth. Rotating off the solvent triethylamine, dry loading by column chromatography to obtain a pale yellow solid 1.86 g (yield 91%).

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

Reference:
Patent; Zhengzhou University; Chen Xiaolan; Sun Kai; Yu Bing; Qu Lingbo; Sun Yuanqiang; (8 pag.)CN108689892; (2018); A;,
Iodide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 16932-44-8, name is 2-Iodo-1,3-dimethoxybenzene, 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 16932-44-8, name: 2-Iodo-1,3-dimethoxybenzene

General procedure: A 2.64 M solution of n-BuLi in hexane (0.4 mL, 1.0 mmol) was added dropwise to a solution of 4 (200 mg, 0.69 mmol) in DME (2 mL) at 0 C under Ar. The mixture was stirred at room temperature for 30 min, before CuCl (109 mg, 1.11 mmol) was added in one portion. Stirring was continued at room temperature for 1 h, before pyridine (0.53 mL, 6.4 mmol) and 3-iodoanisole (234 mg, 1.00 mmol) were added in one portion. Subsequently, the mixture was heated to 100 C for 45 h. After cooling, the reaction was quenched with 10% aq. HCl, before the insoluble materials were removed by filtration through Celite. The filtrate was extracted with AcOEt, and the organic fractions were washed with 10% aq. Na2S2O3 and brine, dried over Na2SO4, and concentrated. Purification by column chromatography on silica gel (eluent: n-hexane) afforded a mixture of 5 and unreacted 3-iodoanisole. A 1 M solution of TBAF in THF (0.79 mL, 0.79 mmol) was added to the mixture in 2 mL of dry THF, before the reaction mixture was stirred for 4 h at room temperature. The reaction was quenched with water and the reaction mixture was extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, and concentrated. Purification by column chromatography on silica gel (eluent: n-hexane to n-hexane/AcOEt = 10/1, v/v) afforded 2b as a colorless solid in 67% yields over two steps.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Kaise, Asako; Ohta, Kiminori; Endo, Yasuyuki; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 257 – 263;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com