Month: March 2021

Electric Literature of 160938-18-1, 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. 160938-18-1 name is 4-Chloro-2-iodo-1-nitrobenzene, 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.

Under an argon atmosphere, to a 500 ml, three neck flask, 20.00 g (170.7 mmol) of indole, 7.67 g (0.1 equiv, 34.1 mmol) of Pd(OAc)2, 94.38 g (2 equiv, 682.9 mmol) of K2CO3, 58.07 g (1.2 equiv, 204.9 mmol) of 4-chloro-2-iodo-1-nitrobenzene and 341 ml of 1,4-dioxane were added in that order, followed by heating, stirring and refluxing for about 24 hours. After cooling to room temperature, the reaction product was filtered with celite to separate insoluble residue, water was added to the remaining reaction product, and an organic layer was separately taken. To an aqueous layer, toluene was added, and an organic layer was extracted once more. The organic layer thus collected was washed with a saline solution and dried with MgSO4. MgSO4 was separated, and the organic layer was concentrated, and then, the crude product thus obtained was separated by silica gel column chromatography (using a mixture solvent of hexane and toluene as a developer) to obtain Intermediate IM-9 (20.95 g, yield 45%) as a white solid compound. A molecular ion peak of m/z=272 was observed by measuring FAB-MS, and from the result, the product was identified as Intermediate IM-9.

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

Reference:
Patent; Samsung Display Co., Ltd.; UNO, Takuya; (126 pag.)US2019/372019; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 2401-21-0,Some common heterocyclic compound, 2401-21-0, name is 1,2-Dichloro-3-iodobenzene, molecular formula is C6H3Cl2I, 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.

PREPARATION 5 A mixture of p-aminopropiophenone (5 g), pyridine (2.7 g), and iodobenzene dichloride (7.5 g) in tetrahydrofuran (150 ml) was stirred for 3 hours at 0¡ã to 5¡ã C. The insoluble materials were filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in chloroform, washed with an aqueous solution of sodium hydrogen sulfite, dried over magnesium sulfate, and concentrated to give an oil (8.8 g). The oil was subjected to column chromatography on silica gel eluding with chloroform. The fractions containing the desired compound were combined and concentrated under reduced pressure. The residual oil was triturated with a mixture of hexane and ethyl acetate to give pale yellow crystals of 4′-amino-3′-chloropropiophenone (1.1 g). mp: 79¡ã to 80¡ã C. IR (Nujol): 3500, 3380, 1670, 1620, 1595 cm-1. NMR (CDCl3, delta): 1.20 (3H, t, J=7 Hz), 2.88 (2H, q, J=7 Hz), 4.50 (2H, broad s), 6.72 (1H, d, J=8 Hz), 7.68 (1H, dd, J=8 Hz, 2 Hz), 7.88 (1H, d, J=2 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dichloro-3-iodobenzene, its application will become more common.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4866091; (1989); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 181765-86-6, These common heterocyclic compound, 181765-86-6, name is Methyl 5-bromo-2-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.

Methyl 5-bromo-2-iodobenzoic acid (25.0 g, 73 mmol) was charged in a 500 mL round bottom flask reactor,4-dibenzofuran boronic acid (18.7 g, 88 mmol), tetrakis (triphenylphosphine) palladium (1.7 g, 0.15 mmol), potassium carbonate (20.2 g, 146.7 mmol)And 125 mL of toluene, 125 mL of tetrahydrofuran, 50 mL of water. The temperature of the reactor was raised to 80 C and stirred for 10 hours.After completion of the reaction, the temperature of the reactor was lowered to room temperature, and the organic layer was extracted with ethyl acetate and separated.The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain (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.; Che Chunxu; Po Xipei; Po Shangyu; Shen Youna; Jin Xida; (130 pag.)CN107207454; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, molecular formula is C3H4F3I, 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: 1,1,1-Trifluoro-3-iodopropane

Example 296A 3-(2-Methoxyethyl)-5-methyl-2,4-dioxo-1-(3,3,3-trifluoropropyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carbaldehyde 341 mg (2.47 mmol) of potassium carbonate were added to a solution of 285 mg (0.98 mmol) of the compound from Ex. 53A in 9 ml of DMF, and the mixture was stirred at RT for 15 min. Then 664 mg (2.96 mmol) of 1,1,1-trifluoro-3-iodopropane were added, and the mixture was stirred at 50 C. for 19 h. The DMF was then very substantially distilled off and the remaining residue was partitioned between semisaturated sodium chloride solution (200 ml) and ethyl acetate (100 ml). The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The residue obtained was chromatographed using a silica gel cartridge (Biotage, 50 g of silica gel, eluent: hexane/ethyl acetate). 254 mg (69% of theory) of the title compound were obtained. 1H-NMR (400 MHz, DMSO-d6, delta/ppm): 10.11 (s, 1H), 4.18 (t, 2H), 4.06 (t, 2H), 3.53-3.48 (m, 2H), 3.24 (s, 3H), 2.84-2.75 (m, 5H). LC/MS (Method 3, ESIpos): Rt=1.10 min, m/z=365 [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 460-37-7, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HAeRTER, Michael; KOSEMUND, Dirk; DELBECK, Martina; KALTHOF, Bernd; WASNAIRE, Pierre; SUessMEIER, Frank; LUSTIG, Klemens; (369 pag.)US2018/65981; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, 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. Product Details of 460-37-7

1,2-Dibromoethane (0.04 ml, 0.51 mmol) was added to a stirred suspension of zinc (0.45 g, 6.82 mmol) in DMF (3.5 ml). The mixture was stirred at 90 C for 30 min. under nitrogen and then chlorotrimethylsilane (0.013 ml, 0.102 mmol) was added. The mixture was stirred at RT for a further 30 min. and then a solution of 3-iodo-l,l,l- trifluoropropane in DMF (2 ml) was added dropwise . The mixture was stirred at 45 C for 2.5 h. and the resulting solution was transferred via syringe to a second flask charged with intermediate 34 (0.144 g, 0.34 mmol) andbis(triphenylphosphine)palladium (II) dichloride (0.024 g, 0.034 mmol) under nitrogen. The mixture was stirred at 40 C for 1 h. and then allowed to cool down to RT. A saturated solution of ammonium chloride was added and the mixture was extracted with EtOAc. The organic layer was separated, washed with a saturated solution of ammonium chloride and brine, dried (Na2S04), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane 0/100 to 100/0). The desired fractions were collected and evaporated in vacuo to yield intermediate 38 (0.07 g, 52%) as a pale brown solid.

The synthetic route of 460-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose, Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; PASTOR-FERNANDEZ, Joaquin; VAN GOOL, Michiel, Luc, Maria; MARTIN-MARTIN, Maria, Luz; VANHOOF, Greta, Constantia, Peter; WO2011/110545; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 40400-15-5, name is 2-(2-Iodophenyl)acetonitrile, molecular formula is C8H6IN, 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-(2-Iodophenyl)acetonitrile

A mixture of 4-((benzyloxy)methyl)-2H-1,2,3-triazole I58 (1.7 g, 9.0 mmol), 2-(2- iodophenyl)acetonitrile (3.0 g, 12.0 mmol), Fe(acac)3 (1.1 g, 3.0 mmol), CuO (720 mg, 0.9 mmol) and Cs2C03 (6.0 g, 18.0 mmol) in DMF (60 mL) was heated at 90 C under N2 for 30 h. The mixture was diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give the title compound (1.4 g, 51 %) as a yellow oil. LCMS-D: Rt 2.87 min; m/z 305.1 [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 40400-15-5, its application will become more common.

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;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 51628-12-7, 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. 51628-12-7, name is 2-(4-Iodophenyl)acetonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 26 Preparation of 2-{4-[4-(1-Methyl-2-{[(methylethyl)sulfonyl]amino}ethoxy)phenyl]phenyl}ethanenitrile. Preparation of 4-(cyanomethyl-phenylboronic acid, pinacol ester. Using the method of Murata, M., et al., Y. J. Org. Chem, 62 6458-6459 (1997), 4-iodophenylacetonitrile (23.9 g, 0.100 mol), Et3N (42 ML, 0.30 mol), acetonitrile (400 ML) and Pd(dppf)2Cl2 catalyst ([1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2) were combined in a 1 L flask and the resulting solution was evacuated and purged with nitrogen three times.The pinacolborane (22 ML, 0.15 mol) was added and the mixture was heated at reflux for 3 h. 1H NMR analysis of an aliquot indicated complete consumption of starting 4-iodophenylacetonitrile.The mixture was cooled to room temperature, concentrated to an oil and taken up in CH2Cl2.This solution was extracted with 0.1 N HCl (3*100 ML) and the organic phase was separated, concentrated and re-dissolved in methyl tert-butyl ether (MTBE).The MTBE solution was passed through a filter packed with silica gel (300 g).The eluant was concentrated to a dark red oil.This oil was extracted with hexanes (500 ML) and the soluble fraction was decanted away from a black oil (5 g). MTBE (5 ML) was added to this oil to give a suspension that was filtered through Celite.This filtrated was combined with the hexanes fraction and the solution was concentrated to an oil.Finally, the oil was re-dissolved in di-isopropyl ether (150 ML) and was diluted with hexanes (400 ML).This mixture was allowed to stand for 2 h, and then filtered to remove a dark precipitate.The resulting amber filtrate was concentrated to an oil, re-dissolved in hexanes (400 ML) and concentrated to 75 ML without added heat.This treatment resulted in the precipitation of the desired intermediate title compound as a golden waxy solid that was air-dried to afford 23.0 g (96.2%): 1H NMR (CDCl3, 300 MHz): delta7.8 (d, 2H); 7.35 (d, 2H); 3.8 (s, 2 H) 1.15 (s, 12H).

The synthetic route of 2-(4-Iodophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Davison, Joshua Zwick; Jones, Winton Dennis; Zarrinmayeh, Hamideh; Zimmerman, Dennis Michael; US2003/225266; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 63279-58-3, name is 1-Bromo-4-iodonaphthalene, 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 63279-58-3, Computed Properties of C10H6BrI

Synthesis Example 1 (Synthesis of a compound (AN-1)); Under the atmosphere of argon, 10 g of 1-bromo-4-iodonaphthalene and 6 g of 4-bromophenylboronic acid which were synthesized in accordance with conventional processes were dissolved into 150 ml of toluene, and 45 ml of a 2M aqueous solution of sodium carbonate was added. Then, 1 g of tetrakistriphenylphosphinepalladium was added, and the resultant mixture was heated under the refluxing condition for 7 hours. After one night, the formed organic layer was extracted with toluene, washed with water and a saturated aqueous solution of sodium chloride. The organic layer was dried with anhydrous sodium sulfate, and the solvent was removed by distillation. The residue was purified in accordance with the silica gel column chromatography (the solvent of development: toluene/hexane), and 6.3 g of 1-bromo-4-(4-bromophenyl)-naphthalene was obtained (the yield: 58percent). The obtained 1-bromo-4-(4-bromophenyl)naphthalene in an amount of 6 g was mixed with 10 g of 10-phenylathracene-9-boronic acid synthesized in accordance with a conventional process and 150 ml of DME. Then, 1.1 g of tetrakistriphenylphosphinepalladium and 50 ml of a 2M aqueous solution of sodium carbonate were added, and the atmosphere was purged with argon. After the resultant mixture was heated under the refluxing condition for 7.5 hours, the mixture was cooled by leaving standing, and formed crystals were separated by filtration. The separated crystals were washed with water, methanol and then heated toluene, and 8.3 g of the object compound (AN-1) was obtained as a light yellow solid substance (the yield: 70percent). When the obtained compound was examined in accordance with the field desorption mass spectroscopy (FDMS), it was found that m/z=708, which agreed with C56H36=708, and the above compound was identified to be Compound AN-1.

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-Bromo-4-iodonaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2003107; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 214279-40-0, name is 2-Iodo-4-methoxy-1-nitrobenzene, molecular formula is C7H6INO3, 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: 214279-40-0

Example 14 Preparation of 2-(5-methoxy-2-nitrophenylthio)-1-(pent-4-ynyl)-1H-imidazo[4,5-c]pyridin-4-amine (Compound 17) A mixture of compound 0113 (150 mg, 0.646 mmol), 1-iodo-5-methoxy-2-nitrobenzene (199 mg, 0.713 mmol), neocuproine hydrate (13 mg, 0.065 mmol), CuI (12 mg, 0.065 mmol) and NaOt-Bu (62 mg, 0.646 mmol) in anhydrous DMF (6 mL) was stirred for 24 h at 110 C. (oil bath) under nitrogen atmosphere. The solvent was removed under high vacuum and the crude purified by column chromatography on silica gel (CH2Cl2/MeOH at 100/1) to obtain target compound 17 as a light yellow solid (60 mg, 24%): LCMS: 384 [M+1]+; 1H NMR (DMSO-d6) delta 1.77 (m, 2H), 2.14 (m, 2H), 2.73 (t, 1H, J=2.4 Hz), 3.69 (s, 3H), 4.24 (t, 2H, J=6.9 Hz), 6.04 (d, 1H, J=2.4 Hz), 6.63 (s, 2H), 6.88 (d 1H, J=6.0 Hz), 7.07 (dd, 1H, J1=2.4 Hz, J2=9.3 Hz), 7.78 (d, 1H, J=6.0 Hz), 8.37 (d, 1H, J=9.3 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 214279-40-0, its application will become more common.

Reference:
Patent; Cai, Xiong; Qian, Changgeng; Zhai, Haixiao; US2008/234314; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 181765-86-6, 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. 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuI (10 mg, 0.05 mmol, 10 mol%), K2CO3 (276 mg, 2.0 mmol), 1,10-phenanthroline (20 mg, 0.10 mmol, 20 mol%) and cyclic thiourea (0.5 mmol), 4 ? Molecular Sieves. The tube was evacuated and backfilled with N2 (this procedure was repeated 3 times). Under a counter flow of N2, methyl-2-iodobenzoate 1 (0.6 mmol) and DMF (2.0 mL) were added by syringe. The mixture was stirred at 100 ?C for 24h. After the reaction was completed, the mixture was directly passed through celite and rinsed with 30 mL of EtOAc. The combined filtrate was concentrated and purified by column chromatography on silica gel to give the pure product.Yellow Yellow solid; mp 152-154 C; 1H NMR (200 MHz, CDCl3) delta 8.31 (d, J = 2.0 Hz, 1H), 7.56 (dd, J1 = 8.6 Hz, J2 = 2.4 Hz, 1H), 7.07 (d, J = 8.6 Hz, 1H), 3.53-3.39 (m, 1H), 3.29-3.15 (m, 1H), 3.07-3.02 (m, 1H), 2.38-2.33 (m, 1H), 1.90-1.86 (m, 2H), 1.74-1.34 (m, 4H); 13C NMR (50 MHz, CDCl3) delta 160.9, 153.8, 136.4, 133.3, 131.1, 126.8, 126.2, 120.6, 71.9, 67.6, 31.0, 30.7, 29.9, 25.4, 24.9 ppm. Anal. Calcd. for C14H13BrN2OS: C 49.86, H 3.89, N 8.31; found: C 50.05, H 4.01, N 8.20; EI-MS: m/z = 336 (M+), 338(M+2).

The chemical industry reduces the impact on the environment during synthesis Methyl 5-bromo-2-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Dingben; Wu, Jiashou; Yang, Jianguo; Huang, Ling; Xiang, Yubo; Bao, Weiliang; Tetrahedron Letters; vol. 53; 52; (2012); p. 7104 – 7107;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com