Category: iodides-buliding-blocks

Electric Literature of 181765-85-5, 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. 181765-85-5, name is Methyl 4-chloro-2-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of (2-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3- yl)methyl)pyrimidin-5-yl)boronic acid (Intermediate 188c, 45 mg, 0.145 mmol) and methyl 4-chloro-2-iodobenzoate (40 mg, 0.135 mmol ) in THF (1.5 mL) was treated with 1.5 M Na2C03 (0.270 mL, 0.405 mmol) followed by PdCl2(dppf) (5.51 mg, 6.75 muiotaetaomicron). The resulting mixture was degassed with N2 for 2 min before the reaction vessel was sealed and irradiated in a microwave reactor at 100 C for 30 min. The cooled reaction mixture was diluted with DCM and extracted. The combined organic layer was washed with brine, dried over MgS04, and concentrated to dryness and the residue purified by ISCO (Hexanes/AcOEt, 0-100%) to afford the title compound (Intermediate 198a, 36 mg, 0.083 mmol, 61.2 % yield) as a yellow oil. LC-MS (Method A5): 2.20 min, [M + H]+ = 436.1 ; FontWeight=”Bold” FontSize=”10″ H NMR (500 MHz, CDC13) delta 8.59 (s, 1H), 8.67 – 8.44 (m, 1H), 8.03 (d, 7=8.5 Hz, 1H), 7.52 (dd, 7=8.5, 2.2 Hz, 1H), 6.90 (s, 1H), 5.78 (s, 2H), 3.72 (s, 3H), 2.87 (q, 7=7.7 Hz, 2H), 2.67 (s, 3H), 2.59 (s, 3H), 1.39 (t, 7=7.6 Hz, 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, Methyl 4-chloro-2-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 5458-84-4,Some common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-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.

Add 1.0 g (3.58 mmol) of 1-iodo-2-methoxy-4-nitrobenzene to a 50 ml two-port bottle and turn on magnetic stirring.Add 15 ml of 95% ethanol at room temperature.Stir for 30min;Adding an appropriate amount of zinc particles to dilute hydrochloric acid for activation;0.8 (12 mmol) of activated zinc particles were sequentially added to the double-mouth bottle.10ml of 20% hydrochloric acid solution,Stirring at room temperature for 72 h;After the reaction,Stop the reaction,The obtained reaction solution was extracted with ethyl acetate.After salt washing, remove the water layer.After the obtained organic phase is distilled under reduced pressure,The dark red solid product, 2-methoxy-4-iodoaniline, 2.18 g was obtained in a yield of 81.23%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-2-methoxy-4-nitrobenzene, its application will become more common.

Reference:
Patent; Ningxia University; Yang Jinhui; Chi Jiurong; Yan Zhiming; Feng Yueji; Wang Shihaozhi; (5 pag.)CN109776331; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 108078-14-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 108078-14-4 as follows.

A 100-mL RB flask was charged with 2-iodo-3-methylbenzoic acid (1. LG, 4.2 mmol), a stirbar, Et20 (15 mL) and DCM (35 mL) and was cooled to-78 oC under an argon atmosphere. trifluoromethanesulfonic acid (250 uL) was added over 30 sec and isobutylene was bubbled into the solution (until the solution became cloudy) using a 8″/20 gauge steel needle. The reaction was stirred for 6 h between-78 AND-20 oC. Solid NAHCO3 (250 mg) was added and the solution was allowed to warm to rt with stirring. After 20 min, the solution was poured into an extraction funnel containing DCM (50 mL) and NA2C03 (2M, 20 mL). The layers were separated and the organic layer was washed with NA2C03 (2M, 2 x 10 mL), water (20 mL), brine (30 mL) and dried over sodium sulfate. Removal of the solvent in vacuo yielded the title compound (1.05 g, 78%) which was used without further purification. 1H-NMR (CDC13) : delta 7.25 (m, 3H), 2.50 (s, 3H), 1.62 (m, 9H).

According to the analysis of related databases, 108078-14-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-DIMENSIONAL PHARMACEUTICALS, INC.; WO2003/99805; (2003); 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. 41860-64-4, name is 4-Fluoro-2-iodo-1-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 41860-64-4

[450] To a solution of 4-fluoro-2-iodo-1-nitrobenzene (2.37 g, 8.9 mmol) in dioxane (10 mL) was added diethylzinc in toluene (13.3 mL, 13.3 mmol) and tetrakis(triphenyl- phosphine)palladium(0) (0.5 g, 0.43 mmol). The mixture was heated to reflux for 30 mm. Upon cooling, the reaction mixture was concentrated in vacuo and the resulting residue was purified by flash column chromatography on silica gel (heptane/EtOAc) to give 2-ethyl-4-fluoro-1-nitrobenzene (A6) as a red oil.

According to the analysis of related databases, 41860-64-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; HUANG, Wei-Sheng; LI, Feng; DALGARNO, David, C.; GONG, Yongjin; ISHCHENKO, Alexey, V.; KOHLMANN, Anna; SHAKESPEARE, William, C.; WEST, Angela, V.; XU, Yongjin; YOUNGSAYE, Willmen; ZHANG, Yun; ZHOU, Tianjun; ZHU, Xiaotian; (444 pag.)WO2015/175632; (2015); A1;,
Iodide – Wikipedia,
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Electric Literature of 17533-08-3, The chemical industry reduces the impact on the environment during synthesis 17533-08-3, name is 1,2,4-Trifluoro-5-iodobenzene, I believe this compound will play a more active role in future production and life.

General procedure: preparation of 3,3,3-trifluoro-2-hydroxy-1-morpholino-2-phenylpropan-1-one 8b (Table 2, entry 1). To a solution of phenyl iodide 5a (300 lL, 2.68 mmol)in THF (4 mL) at 0 C, isopropylmagnesium chloride in THF (1338 lL,2.68 mmol, 2 M) was added dropwise. After stirring at 0 C for 1 h, a solutionof methyl trifluoropyruvate 7a (273 lL, 2.68 mmol) in THF (3 mL) was addeddropwise at 78 C. The mixture was stirred at 78 C for 1 h and thenwarmed to 0 C, morpholine 6b (350 lL, 4.01 mmol) and isopropylmagnesiumchloride (2.0 mL, 4.01 mmol, 2 M) were added dropwise. At the end of theaddition, the external cooling was removed, and the reaction was aged at roomtemperature overnight. At 0 C, the reaction mixture was quenched with slowaddition of satd. NH4Cl and extracted with EtOAc. The combined organic layerswere dried over anhydrous Na2SO4, filtered, and concentrated in vacuo.Purification by flash chromatography (0-60% EtOAc/hexane) provided thedesired amide

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, 1,2,4-Trifluoro-5-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Meng, Zhaoyang; Butcher, William E.; Tetrahedron Letters; vol. 54; 37; (2013); p. 5133 – 5136;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 56404-21-8, 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. 56404-21-8, name is 1-Iodo-2,4-dimethyl-3-nitrobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Scheme 4, Step B: To a 2 L Parr autoclave with mechanical stirring is added 1-iodo-2,4-dimethyl-3-nitro-benzene (70 g, 252.7 mmol), Pd(OAc)2 (2.8 g, 12.6 mmol),1 ,4-bis( diphenylphosphino )butane ( 6.5 g, 15.2 mmol), acetonitrile ( 462 mL ),triethylamine (88.2 mL), and methanol (280 mL). The Parr autoclave is sealed, purgedand pressurized with CO to 551.6 kPa (80 psig). The mixture is heated to 100C for 2hours. The mixture is cooled to ambient temperature and then vented. The mixture isthen concentrated to dryness under reduced pressure. Ethyl acetate (300 mL) and water(300 mL) are added. The layers are separated and the aqueous layer discarded. The organic layer is dried over MgS04, filtered, and concentrated to dryness to afford the title20compound as a red oil which crystallizes upon standing (52 g, 98 %). 1 H NMR (300.13MHz, CDCl3): o 7.89 (d, J= 8.2 Hz, 1H), 7.19 (d, J= 8.2 Hz, 1H), 3.91 (s, 3H), 2.49 (s,3H), 2.33 (s, 3H).

The synthetic route of 1-Iodo-2,4-dimethyl-3-nitrobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; BLANCO-PILLADO, Maria-Jesus; VETMAN, Tatiana Natali; FISHER, Matthew Joseph; KUKLISH, Steven Lee; WO2014/4230; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 61203-48-3, 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. 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

Example 2.a. N-(6,7-Methylenedioxycinnolin-4-yl)-N-(N,N-diethylaminoethyl)- 2-iodo-4,5-dimethoxybenzamide: Prepared from N’-(6,7-Methylenedioxycinnolin-4- yl)-N,N-diethylethane-l,2-diamine (640 mg, 2.2 mmol); (87% yield); reaction time 16 h; IR (CHC13) 1656; 1H NMR (CDC13) delta 0.92 (t, 6H, J=7.0), 2.50 (q, 4H, J=7.0), 2.80 (t, 2H, J=6.8), 3.39 (s, 3H), 3.71 (s, 3H), 3.94 (m, 1H), 4.41 (m, 1H), 6.21 (d, 2H, J=1.4), 6.39 (s, 1H), 7.01 (s, 1H), 7.39 (s, 1H), 7.64 (s, 1H), 9.11 (s, 1H); 13C NMR (CDC13) delta 11.6, 46.9, 47.8, 51.1, 55.7, 56.1, 82.9, 96.9, 102.9, 105.5, 110.9, 122.1, 122.9, 133.0, 136.5, 144.9, 148.3, 150.1, 150.9, 151.7, 152.3, 169.8; HRMS calcd for C24H2705N4IH: 579.1105; found: 579.1105.

The chemical industry reduces the impact on the environment during synthesis 2-Iodo-4,5-dimethoxybenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENZYME CORPORATION; TEICHER, Beverly, A.; SCHMID, Steven, M.; WO2012/15901; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

175278-30-5, name is 4-Bromo-2-ethyl-1-iodobenzene, 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. SDS of cas: 175278-30-5

20 g (64.3 mmol) of 1-iodo-2-ethyl-4-bromobenzene and 12 g (64.3 mmol) of 4-n-hexylphenylacetylene are initially introduced into 300 ml of triethylamine and 250 mg (1.3 mmol) Of copper (I) iodide and 900 mg (1.3 mmol) of bis (triphenylphosphine) palladium (II) chloride are added and the mixture is stirred at RT for 3 h and then refluxed for 1 h.Cool the batch, add water and heptane, and separate the phases. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue is purified by column chromatography (SiO 2, heptane); the product is obtained as a colorless oil.

The synthetic route of 175278-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; JASPER, CHRISTIAN; MONTENEGRO, ELVIRA; PAULUTH, DETLEF; REIFFENRATH, VOLKER; MANABE, ATSUTAKA; (43 pag.)JP6218607; (2017); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 689260-53-5, These common heterocyclic compound, 689260-53-5, name is 2-Bromo-5-iodo-1,3-dimethylbenzene, 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.

Step 1: 1-(4-(4-Bromo-3,5-dimethylphenyl)-1H-pyrazol-1-yl)-2-methylpropan-2-ol A mixture of 2-bromo-5-iodo-1,3-dimethylbenzene (1.00 g), 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol (1.11 g), and 2 M aqueous Na2CO3 solution (4.0 mL) in N,N-dimethylformamide is purged with argon for 3 min. [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloromethane complex (85 mg) is added and the mixture is stirred at 60 C. for 3 h. After cooling to room temperature the mixture is diluted with water and ethyl acetate. The organic phase is washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is purified by HPLC on reversed phase to give the title compound. LC (method 11): tR=1.12 min; Mass spectrum (ESI+): m/z=323, 325 [M+H]+.

The synthetic route of 689260-53-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; US2013/252937; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 34270-90-1 as follows. SDS of cas: 34270-90-1

General procedure: Step (1): Carry out substitution reaction using dimethyl 4-hydroxyphthalate as raw material;Specifically: put dimethyl 4-hydroxyphthalate and dihalo compound in anhydrous acetonitrile,Add an appropriate amount of cesium carbonate solid and stir at 80 C for 12 hours.The solid was removed by filtration, the filtrate was spin-dried, and purified by silica gel chromatography using petroleum ether / ethyl acetate or dichloromethane / methanol.

According to the analysis of related databases, 34270-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Peking University; Lei Xiaoguang; Tang Yuliang; Dong Mengqiu; Wang Jianhua; (26 pag.)CN110981715; (2020); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com