Tag: M.W=200-300

Synthetic Route of 2265-92-1, A common heterocyclic compound, 2265-92-1, name is 1,4-Difluoro-2-iodobenzene, molecular formula is C6H3F2I, 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 2: 2-tert-Butyl-6-(2,5-difluoro-phenylethynyl)-[1,2,4]triazolo[1,5-a]pyrimidine 2-tert-Butyl-6-trimethylsilanylethynyl-[1,2,4]triazolo[1,5-a]pyrimidine (example 43, step 1) (100 mg, 0.37 mmol) was dissolved in DMF (1 ml). 1,4-Difluoro-2-iodobenzene (176 mg, 0.73 mmol, 2 equiv.), Et3N (150 mul, 1.1 mmol, 3 equiv.), Bis-(triphenylphosphine)-palladium(II) dichloride (13 mg, 0.02 mmol, 0.05 equiv.), triphenylphosphine (3 mg, 0.011 mmol, 0.03 equiv.) and copper(I) iodide (2 mg, 0.011, 0.03 equiv.) were added under nitrogen and the mixture was heated to 80 C. TBAF 1M in THF (440 mul, 0.44 mmol, 1.2 equiv.) was added dropwise in 20 minutes at 80 C. The reaction mixture was stirred for 5 minutes at 80 C. The reaction mixture was evaporated and extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a 20 g silica gel column and eluting with heptane:ethyl acetate 100:0->50:50. The desired 2-tert-butyl-6-(2,5-difluoro-phenylethynyl)-[1,2,4]triazolo[1,5-a]pyrimidine (73 mg, 64% yield) was obtained as a light yellow solid, MS: m/e=313.1 (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:
Patent; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindermann, Lothar; Stadler, Heinz; Vieira, Eric; US2011/152257; (2011); A1;,
Iodide – Wikipedia,
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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. 74534-15-9, name is 1-Chloro-2-iodo-4-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Chloro-2-iodo-4-nitrobenzene

Triethylamine (0.2ml, 1.43mmol) was added to a suspension of 1-Chloro-2- iodo-4-nitro-benzene 69 (Step 1) (100mg, 0.354mrnol), 1-ethynyl-2-fluorobenzene (100mg, 0.832mmol), copper iodide (100mg, 0.525mmol),Pd(PPh3)2Cl2 (100mg, 0.142mmol) in dimethylformamide (2ml) at room temperature, then stirred at 700C for 2 hours. Reaction was cooled to room temperature and extracted with ether (50ml), washed with v/ater(20ml), dried (MgSO4), filtered and solvent evaporated yielding a residue which chromatographed on silica gel eluting with 20% v/v MeCI2/hexanes yielding title product 70 as pale yellow solid (80mg,82%).

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 74534-15-9.

Reference:
Patent; SCHERING CORPORATION; WO2007/70398; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 460-37-7,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.

5.0 g (21.0 mmol) of the compound from Ex. 48A and 10.3 g (31.5 mmol) of caesium carbonate were stirred in 50 ml of DMF at RT for 15 min, before 3.7 ml (31.5 mmol) of 1,1,1-trifluoro-3-iodopropane were added. Subsequently, the reaction mixture was stirred at a temperature of 60 C. for about 18 h. After cooling to RT, the mixture was diluted with about 200 ml of ethyl acetate and washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate, the mixture was filtered and the filtrate was concentrated to dryness. The crude product was purified by MPLC (Biotage cartridge, 80 g of silica gel, eluent: cyclohexane/ethyl acetate 3:1). Concentration and drying of the product fractions gave 4.8 g (62% of theory) of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,1-Trifluoro-3-iodopropane, 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,
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Related Products of 5876-51-7, A common heterocyclic compound, 5876-51-7, name is 5-Iodobenzo[d][1,3]dioxole, molecular formula is C7H5IO2, 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.

[00255] The 4-phenyl-1,3,2-dioxaborolane was first prepared by reaction of 236 mg phenyl-1,2-ethanediol (1.7 mmol) with borane dimethylsulfide adduct (0.15 ml, 1.5 mmol) in 2 ml of dioxane. A stock solution of the catalyst in dioxane was made by heating 250 mg PdCl2[dppf].CH2Cl2 with triethylamine (4.5 ml) at 80 C. for 20 h in 40 ml dioxane. To this solution was added 2.48 g (10 mmol) of 1-iodo-3,4-methylenedioxybenzene. 4.8 ml of this reaction solution was then placed in the reaction tube containing the borane ester. The mixture was heated for 20 h at 80 C. and then an aliquot was removed, dissolved in some ethyl acetate containing a little of the diol and shaken with 10% brine solution. After drying with MgSO4, the gc was measured. One major peak, of retention time 15.7 mins was found. This was shown by gc/ms to be the desired product.

The synthetic route of 5876-51-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 101335-11-9, A common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, 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 15 mL reaction tube, ArI (1 mmol), (i-Pr)2NEt (2 mmol),DMF (0.5 mL) and 5 mg of PdCl2/PANI were added. The reactionmixture was stirred at 140 C under air for 2.5 h. After the reaction,the catalyst was isolated by centrifugalization, washed by deionized water and ethanol, vacuum dried at 60 C and then reused in the next round of reaction. Organic phase was collected, add saturatedsalt water (2 mL), extracted with ethyl acetate (15 mL), thenthe organic phase was dried with anhydrous Na2SO4. The productwas separated and purified by silica gel column chromatography(eluent: petroleum ether).

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Yanping; Liu, Wanyi; Song, Manrong; Sun, Yanyan; Wang, Gang; Wu, Zhiqiang; Zhan, Haijuan; Journal of Catalysis; vol. 384; (2020); p. 177 – 188;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 696-41-3, name is 3-Iodobenzaldehyde, molecular formula is C7H5IO, 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. Safety of 3-Iodobenzaldehyde

The mixture of 3-iodobenzaldehyde (1, 4.00 g, 17.2 mmol) in Deoxo-Fluor (12 mL) was stirred at room temperature overnight. Then it was diluted with dichloromethane (150 mL) followed by dropwise addition of 10% aqueous solution of potassium carbonate (200 mL) at 0 C. Phases were separated; organic layer was dried over anhydrous sodium sul- fate, filtered and evaporated. The residue was subjected to flash column chromatog- raphy (Silicagel 60, 0.040-0.063 mm; eluent: cyclohexane) to afford l-(difluoromethyl)- 3-iodobenzene (2) as colorless oil. Yield : 3.22 g (74%). RF (Si02, cyclohexane) : 0.50. *H NMR spectrum (300 MHz, CDCI3, deltaEta) : 7.89-7.85 (m, 1 H); 7.85-7.79 (m, 1 H); 7.52- 7.46 (m, 1 H); 7.24-7.17 (m, 1 H); 6.59 (t, J = 56.2 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 696-41-3, its application will become more common.

Reference:
Patent; NOVO NORDISK A/S; KRUSE, Thomas; HANSEN, Mikael, Kofoed; MUeNZEL, Martin, Werner, Borchsenius; THØGERSEN, Henning; SAUERBERG, Per; RASMUSSEN, Jakob, Ewald; BEHRENS, Carsten; HØEG-JENSEN, Thomas; BAL?ANEK, Vojtech; DROBNAKOVA, Zuzana; DRO?, Ladislav; HAVRANEK, Miroslav; KOTEK, Vladislav; ?TENGL, Milan; ?NAJDR, Ivan; VANOVA, Hana; (202 pag.)WO2019/92125; (2019); A1;,
Iodide – Wikipedia,
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These common heterocyclic compound, 645-00-1, name is 1-Iodo-3-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. Product Details of 645-00-1

General procedure: A 20mL scintillation vial was charged with a Teflon stir bar, copper complex (0.1mmol), 76 potassium carbonate (0.75mmol), aryl iodide (0.5mmol), 77 phenylacetylene (0.75mmol) in 5mL non-anhydrous DMF in air. The vial was sealed and placed in an oil bath with pre-adjusted temperature at 135-140C. After the allowed time, the reaction mixture was cooled down, diluted with 25-30mL ethyl acetate, and filtered through a pad of silica gel. The solvent was then removed under vacuum and the residue was purified by column chromatography using mixtures of hexane and ethyl acetate to obtain analytically pure product.

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

Reference:
Article; Domyati, Doaa; Latifi, Reza; Tahsini, Laleh; Journal of Organometallic Chemistry; vol. 860; (2018); p. 98 – 105;,
Iodide – Wikipedia,
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29632-73-3, name is 2-Bromo-4-iodoaniline, 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. COA of Formula: C6H5BrIN

2-bromo-4-iodoaniline (500 mg, 1.68 mmol) was added to an eggplant-shaped flask, and 10 mL of dry N,N-dimethylformamide was added. Sodium hydride (110 mg, 2.52 mmol) was added, and 1-bromo-2-methoxyethane (350 mg, 2.52 mmol). Heat to 100 C and stir overnight. After completion of the reaction, asaturated sodium chloride solution was added, it was extracted with ethyl acetate three times, and the organic phases were combined, dried over anhydrous sodiumPurified on a silica gel column to obtain the target compound 576 mg.

The synthetic route of 29632-73-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
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. 202865-85-8, name is 1-Bromo-4-iodo-2-methylbenzene, A new synthetic method of this compound is introduced below., Product Details of 202865-85-8

Example N22, Step aA solution of l-bromo-4-iodo-2-methylbenzene (5.0 g, 16.83 mmol) in dioxane (75 mL) was purged with 2 for 10 minutes. Then PdCl2(Pli3P)2 (428 mg 0.609 mmol) and tri-n-butyl(l-ethoxyvinyl)stanane (5.94 mL, 17.59 mmol) was added, and the reaction mixture was purged with 2 for 10 minutes and heated at 80 C for overnight. Water (25 mL) was added to the reaction mixture and cooled to 0 C, NBS (3 g, 17.1 mmol) was added and the mixture was stirred for 30 minutes. The volatile component was removed under reduced pressure, and water was added to the resulting residue and it was extracted with DCM (3 x 100 mL). The combined organic extract was dried over Na2S04 and concentrated in vacuo. The crude was purified by flash chromatography (ISCO; EtOAc: petroleum ether, 2:98) to afford ketone N22a (2.6 g). ¾ NMR (CDCI3, delta = 7.26 ppm, 400 MHz): delta 7.84 (d, J = 0.8, 1H), 7.65-7.62 (m, 2H), 4.32 (s, 2H), 2.48 (s, 3H).

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; BRISTOL-MYERS SQUIBB COMPANY; BELEMA, Makonen; HEWAWASAM, Piyasena; WO2012/39717; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, molecular formula is C7H4F3I, 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. Safety of 1-Iodo-3-(trifluoromethyl)benzene

General procedure: A mixture of thiol (0.5 mmol), aryl halide (0.6mmol), CuI (5 mol%, 4 mg), DABCO (10 mol%, 5.6 mg) K2CO3(2 equiv, 138 mg) and DME (3 ml) were added to an oven-dried sealed tube equipped with a stirring bar under nitrogen. The sealed tube was stirred in a preheated oil bath at 120 oC for 12 h. After being cooled to room temperature, the mixture was diluted with ethyl acetate(30 ml) and washed with saturated aqueous NaCl solution (3 x 15 ml).The organic phase was dried with anhydrous Na2SO4,filtered, and the solvent was removed under vacuum. The crude residue was purified by column chromatography on silica gel using ethyl acetate/hexanes as the eluent to give the desired sulphides.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 401-81-0, its application will become more common.

Reference:
Article; Thomas, Anns Maria; Asha, Sujatha; Sindhu; Anilkumar, Gopinathan; Tetrahedron Letters; vol. 56; 47; (2015); p. 6560 – 6564;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com