Month: August 2021

Reference of 2265-91-0, 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 2265-91-0 as follows.

Step 1: tert-Butyl 4-(3,5-difluorophenyl) piperazine-1-carboxylate A solution of tert-butyl-piperazine-1-carboxylate (1.024 g, 5.5 mmol), 1,3-difluoro-5-iodobenzene (1.58 g, 6.6 mmol), t-BuONa (790 mg, 8.25 mmol), BINAP (137 mg, 0.22 mmol), Pd2(dba)3 (100 mg, 0.11 mmol) in dry toluene (40 mL) was stirred under N2 at 80 C. for 16 hrs. The reaction mixture was concentrated and the residue was purified by chromatography (silica, EtOAc/PE=1/10) to afford 1-(3,5-difluorophenyl)piperazine (1.5 g, 5.03 mmol, 91%) as a yellow oil. ESI-MS (EI+, m/z): 243.2 [M-55]+.

According to the analysis of related databases, 2265-91-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; O’Neill, David John; Saiah, Eddine; Kang, Seong Woo Anthony; Brearley, Andrew; Bentley, Jonathan; (136 pag.)US2019/389843; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 104539-21-1, A common heterocyclic compound, 104539-21-1, name is 1-Iodo-2-(2-methoxyethoxy)ethane, molecular formula is C5H11IO2, 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.

STR45 77 mg (0.158 mmol) of Compound 28 synthesised in Example 23 was dissolved in 2 ml of anhydrous DMF. To this solution, 255 mg (1.11 mmol) of 1-iodo-2-(2-methoxyethoxy)ethane and then 109 mg (0.79 mmol) of potassium carbonate were added. This reaction mixture was stirred in an atmosphere of argon at room temperature for 5 hours. The reaction mixture was then added to water. The mixture was then extracted with ethyl acetate. The extract layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated. The residue was chromatographed on silica gel and eluted with a mixed solvent of ethyl acetate and hexane (2:1), whereby ethyl (E)-7-[6-(4′-fluorophenyl)-2,3-dihydro -7-[2-(2-methoxyethoxy) ethoxy ]-2,2-dimethyl -4-(propan-2-yl)benzo[b]furan-5-yl ]-3,5-dihydroxy-6-heptenoate (Compound 30) was obtained in a yield of 70 mg (75.3%). Melting point: 97.5~98.5 C. (colorless, fine particle-shaped crystals, recrystallized from a mixed solvent of ethyl acetate and hexane) 1 H-NMR (300MHz, CDCl3) delta 1.21 (d, J=7. 1Hz, 3H), 1.22 (d, J=7.1Hz, 3H), 1.28 (t, J=7.2Hz, 3H), 1.10-1.44 (m, 2H), 1.50 (s, 6H), 2.32-2.46 (m, 2H), 2.64-2.68 (m, 1H), 3.13 (s, 2H), 3.27 (hept, J=7.1Hz, 1H), 3.34 (s, 3H), 3.38 (s, 4H), 3.45-3.50 (m, 2H), 3.55-3.60 (m, 1H), 3.94-3.99 (m, 2H), 3.99-4.10 (m, 1H), 4.18 (q, J=7.2Hz, 2H), 4.20-4.31 (m, 1H), 5.09 (dd, J=16.0 and 6.6Hz, 1H), 6.33 (dd, J=16.0 and 1.0Hz, 1H), 6.94-7.04 (m, 2H), 7.08-7.16 (m, 2H)ppm. IR (KBr): 3432, 2972, 2936, 2880, 1722, 1596 cm-1. Mass (m/z, %): 588 (M+, 100), 570 (76), 454 (23), 413 (17), 311 (17), 269 (11), 103 (36), 59 (40).

The synthetic route of 104539-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujirebio Inc.; US5523460; (1996); A;,
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. 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Iodo-3-(trifluoromethyl)benzene

General procedure: A flask was charged with i-PrMgCl·LiCl (4.63 mL, 1.0807 M) cooled to-20 C, and then neat iodobenzene (1.020 g, 5 mmol) was added. The reaction mixture was stirred for 30 min, and then, a ZnCl2 solution inTHF (5.5 mL, 1 M) was added. The mixture was stirred for 15 min and allowed to warm to r.t. over 30 min. A flask charged with 3e (242 mg, 1 mmol), Pd(dba)2 (30 mg, 5 mol%),and SPhos (40 mg, 10 mol%) was evacuated and back-filled with argon,and then, THF (1.5 mL) was added, and the reaction mixture wasstirred for 5 min. Next, the organozinc reagent PhZnCl (2.10 mL,0.5226 M) was added, and the mixture was stirred for 30 min. Themixture was quenched with aq NH4Cl (0.5 mL), diluted with Et2O (30mL), and the organic layer was washed with sat. aq NH4Cl (2 × 30 mL)and brine (30 mL). The organic layer was dried (MgSO4) and evaporated,and the residue was purified by column chromatography (eluent:CH2Cl2).

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; Dubovik, Julia; Bredihhin, Aleksei; Synthesis; vol. 47; 4; (2015); p. 538 – 548;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 34270-90-1, These common heterocyclic compound, 34270-90-1, name is 1-Iodo-2-(2-iodoethoxy)ethane, 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 :NaH (60% in oil, 975 mg, 24.38 mmol) is washed with pentane (3x) and then suspended in dry THF (10 mL). A solution of 4,4-dimethyl cyclohexanone (1.02 g, 8.12 mmol, Combi-Blocks) in THF (5 mL) is added, followed by bis-2-iodoethyl ether (1.25 mL, 8.80 mmol). The reaction mixture is heated to 65C. When an exothermic reaction occurs, external heating is stopped and the reaction mixture is stirred for 1.5 h. The reaction mixture is heated at reflux for 30 min, and then is poured into water and extracted with ether. The aqueous phase is acidified to pH 6 with 1 M HCI and extracted with ether (2x). The filtrate is dried over anhydrous Na2S04, concentrated under reduced pressure and purified by Combiflash (90:10Hex EtOAc) to afford 6a1.

The synthetic route of 34270-90-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BROCHU, Christian; GRAND-MAITRE, Chantal; FADER, Lee; KUHN, Cyrille; BERTRAND-LAPERLE, Megan; PESANT, Marc; WO2013/26163; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, 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. Formula: C2H2IN

The compound obtained in Example 21 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours by heating. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and to the residue were added water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of [4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile and [4-(2-chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile as yellow oil. These two regioisomers (4.78 g, 92%) were used in the next reaction step without separation.[4-(2-Chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.29 (s, 3H), 3.71 (s, 3H), 5.19 (s, 2H), 6.73 (s, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.06 (d, J=4.4 Hz, 1H), 7.26 (s, 1H), 7.79 (s, 1H), 8.24 (d, J=4.8 Hz, 1H); 13C NMR (CDCl3) delta 21.53, 39.97, 55.29, 110.91, 111.12, 113.65, 115.67, 118.75, 121.59, 121.65, 122.78, 130.58, 132.37, 140.16, 143.28, 149.68, 151.45, 151.79, 159.71, 162.33.[4-(2-Chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.83 (s, 3H), 4.94 (s, 2H), 6.63 (s, 1H), 6.74 (s, 1H), 6.92-6.96 (m, 2H), 7.19 (s, 1H), 7.93 (s, 1H), 8.17 (d, J=5.2 Hz, 1H); 13C NMR (CDCl3) delta 21.56, 37.78, 55.48, 112.15, 113.91, 117.08, 118.16, 119.88, 121.36, 122.48, 128.46, 139.57, 141.60, 142.19, 142.85, 149.78, 151.95, 160.48.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 22 (320 mg, 0.95 mmol), 3-acetylphenylboronic acid (0.19 g, 1.13 mmol), dichlorobis(triphenylphosphine)palladium (II) (33 mg, 0.05 mmol) and potassium carbonate (131 mg, 0.95 mmol), and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:2, v/v): (96 mg, 77%); m.p. 65-66 C.; 1H NMR (CDCl3) delta 2.39 (s, 3H), 2.62 (s, 3H), 3.79 (s, 3H), 4.96 (s, 2H), 6.74 (s, 1H), 6.80 (s, 1H), 6.95 (s, 1H), 7.10 (bs, 1H), 7.50 (t, J=7.5 Hz, 1H), 7.56 (s, 1H), 7.94-8.00 (m, 3H), 8.29 (s, 1H), 8.52 (d, J=4.2 Hz, 1H); 13C NMR (CDCl3) delta 21.59, 26.78, 37.77, 55.78, 112.33, 114.14, 116.93, 118.18, 119.32, 120.14, 122.64, 126.60, 128.68, 129.01, 131.39, 137.53, 139.59, 139.72, 140.66, 141.54, 141.93, 150.05, 156.54, 160.45, 197.89.

The synthetic route of 2-Iodoacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 108078-14-4, 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. 108078-14-4 name is 2-Iodo-3-methylbenzoic acid, 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.

a (2-Iodo-3-methyl-phenyl)-methanol Thionyl chloride (6 mL) was added over 1 min to a 0 C. solution of 2-iodo-3-methyl benzoic acid (3.0 g, 11.4 mmol) in DCM (10 mL). The solution was stirred for 24 h at rt and the volatile components were removed in vacuo. A portion of the crude acid chloride (955 mg) was dissolved in THF (15 mL) and NaBH4 (380 mg, 10 mmol) was added. After stirring for 90 min, multiple spots were evident by TLC analysis. The reaction mixture was cooled to -78 C. and solid LiAlH4 (300 mg, 7.91 mmol) was added. The reaction was stirred for 30 min, after which TLC analysis showed one major spot. The reaction was quenched by addition of EtOAc (10 mL) and was slowly poured into a vigorously stirred solution of HCl (1M, 30 mL). EtOAc (70 mL) was added, the layers were separated, and the organic layer was washed with NaHCO3 (3*15 mL), water (15 mL), brine (40 mL), and was dried over sodium sulfate. Removal of the solvent in vacuo yielded the title compound (752 mg, 89%) as a thick oil which was used without further purification. 1H-NMR (CDCl3): delta 7.27 (m, 2H), 7.20 (m, 2H), 4.74 (m, 2H), 2.50 (s, 3H), 2.0 (br s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-3-methylbenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; 3-Dimensional Pharmaceuticals, Inc.; US2004/9995; (2004); A1;,
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. 612-55-5, name is 2-Iodonaphthalene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C10H7I

General procedure: For a typical reaction, a Vapourtec 2R+ Series was used as the platform with a Vapourtec Gas/Liquid Membrane Reactor to load the carbon monoxide. The HPLC pump were both set at 0.125 mL/min, temperature of the reactor at 110 C, pressure of CO at 15 bar with a back pressure regulator of 250 psi (17.24 bar). The system was left running for 2 h to reach steady state after which time the flow streams were switched to pass from the loops where the substrates and catalysts were loaded. The first loop (5 mL) was filled with a solution of palladium acetate (20 mg, 0.08 mmol), triphenylphosphine (48 mg, 0.168 mmol) in 6 mL of 1,4-dioxane while the second loop (5 mL) was filled with a solution made from the ortho-substituted iodoarene substrate (1.68 mmol), triethylamine (0.272 g, 0.374 mL, 2.69 mmol) and water (0.505 g, 28 mmol) in 5.8 mL of 1,4-dioxane. An Omnifit column filled with 1.71 cm3 (r = 0.33 cm, h = 5.00 cm) of cotton was positioned just before the back pressure regulator to trap any particulate matter formed to avoid blocking of the back pressure regulator. After the substrates were passed through the system, the outlet of the flow stream was directed into a receptacle where the excess carbon monoxide gas was vented off in the fume cupboard. The reaction mixture was then evaporated to dryness, ethyl acetate (25 mL) and sodium carbonate solution (2 M, 10 mL) were added and transferred to a separating funnel. After collecting the aqueous layer, the organic layer was extracted with sodium carbonate solution (2 M, 2 × 10 mL). The combined aqueous layers were acidified by the addition of 2 M HCl solution which was then extracted with ethyl acetate (3 x 25 mL). The organic layer was dried over sodium sulfate, and the solvent evaporated under vacuum to give the crude product as a solid. The crude product was then recrystallised from the appropriate solvent.

The synthetic route of 612-55-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mallia, Carl J.; Walter, Gary C.; Baxendale, Ian R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1503 – 1511;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 51628-12-7, name is 2-(4-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. Formula: C8H6IN

A solution of NaOH (50%, 8 ml) was added dropwise to a mixture of compound LII-1 (2 g, 8.23 mmol), l-bromo-2-chloroethane (2.37 g, 16.5 mmol) and benzyl- triethylammonium chloride (0.094 g, 0.41 mmol) at room temperature. The reaction mixture was stirred and heated to 60 C overnight. Reaction was monitored by TLC. The reaction mixture was quenched with water and extracted with CH2CI2. The organic layer was washed two times with dilute hydrochloric acid, dried over Na2S04 and concentrated. The residue was purified by column chromatography (PE: EA = 50: 1-20: 1) to give compound LII-2 (1.35 g, yield: 61%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51628-12-7, its application will become more common.

Reference:
Patent; INTERMUNE, INC.; BUCKMAN, Brad, O.; NICHOLAS, John, B.; EMAYAN, Kumaraswamy; SEIWERT, Scott, D.; WO2013/25733; (2013); A1;,
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. 444-29-1, name is 1-Iodo-2-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Safety of 1-Iodo-2-(trifluoromethyl)benzene

General procedure: A 50mL round-bottomed flask equipped with a gas inlet tube, a reflux condenser, and a magnetic stirring bar was charged with MCM-41-S-PdCl2 (173mg, 0.05 mmol Pd), aryl halide (5.0 mmol) and HCOONa (7.5 mmol). The flask was flushed with carbon monoxide. DMF (5 mL) was added by syringe and a slow stream of CO was passed into the suspension. The mixture was vigorously stirred at 100?110°C for 4?24h, cooled to room temperature, and diluted with diethyl ether (50 mL). The palladium catalyst was separated from the mixture by filtration, washed with distilled water (2×10 mL), ethanol (2×10 mL) and ether (2×10 mL) and reused in the next run. The ethereal solution was washed with water (3×20mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane?ethyl acetate=10:1). (0008) All formylation products were characterized by comparison of their spectra and physical data with authentic samples. IR spectra were determined on a Perkin-Elmer 683 instrument. 1H NMR (400MHz) and 13C NMR (100MHz) spectra were recorded on a Bruker Avance 400MHz spectrometer with TMS as an internal standard and CDCl3 as solvent.

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; Hao, Wenyan; Ding, Guodong; Cai, Mingzhong; Catalysis Communications; vol. 51; (2014); p. 53 – 57;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 31827-94-8, 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. 31827-94-8, name is 2-Bromo-1-(4-iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The appropriate carbonyl compound (50 mmol) was dissolved in 50 mL of ethanol and magnetically stirred with an equimolar quantity of thiosemicarbazide for 24 h at room temperature with catalytic amounts of acetic acid. The desired thiosemicarbazone precipitated from reaction mixture, was filtered, crystallized from suitable solvent, and dried. Equimolar quantities of 4-iodo-acetophenone and bromine, both dissolved in chloroform, were stirred for 4 h at room temperature until the presence of HBr disappeared. The solution was evaporated under vacuum and the obtained pale yellow solid was washed with petroleum ether to give alpha-bromo-4-iodo-acetophenone in good yield (94%). Equimolar amounts of the prepared thiosemicarbazone (50 mmol) and alpha-bromo-4-iodo-acetophenone (50 mmol), both suspended in 50 mL of ethanol, were reacted at room temperature under magnetic stirring for 10 h. The precipitate was filtered and purified by chromatography to give compounds 1-25 in high yield.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-(4-iodophenyl)ethanone. I believe this compound will play a more active role in future production and life.

Reference:
Article; Secci, Daniela; Bizzarri, Bruna; Bolasco, Adriana; Carradori, Simone; D’Ascenzio, Melissa; Rivanera, Daniela; Mari, Emanuela; Polletta, Lucia; Zicari, Alessandra; European Journal of Medicinal Chemistry; vol. 53; (2012); p. 246 – 253;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com