Month: May 2021

Electric Literature of 1542-34-3,Some common heterocyclic compound, 1542-34-3, name is 3,5-Difluoro-4-iodoaniline, molecular formula is C6H4F2IN, 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 suspension of 3,Sdifluoro4-4odoaniline (14.7 g, 55.9 mmol), CuT (0.745 g, 3.91 mmoi), bis(triphenyiphosphine)paiiadium(ll) dichioride (1 .59 g, 2,24 mrnoi), methyl 4 ethynylbenzoate (9.05 , 55.9 mmol), TEA (114 mL) and THF (44.1 mL) is stirred at 60Cfor 3 hr. The mixture is cooled to RT and the solvent evaporated to dryness under reduced pressure. EtOAc (10() mL) and H2() (100 mL) are added, and the resulting solid is filtered over diatornaceous earth. The organic layer from the filtrate is separated, dried over MgSO4, and evaporated to dryness under reduced pressure. A 1:1 mixture of DCM:heptane (400 nI) is added to the resulting residue and the mixture is stirred at RT overnight. The resultingsolid is collected by filtration and dried under vacuum to obtain the title compound (8.0 g,45.8% yield) as a brown solid. ?H NMR (300 MHz, DMSO-d6) oe 3.86 (s, 3H), 6.266.37 (m,4H), 7.59 (d, J = 8.2 Hz, 2H), 7.96 (d, J = 8.5 Hz, 2H).

The synthetic route of 1542-34-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; COATES, David Andrew; FALES, Kevin Robert; PETERSON, Jeffrey Alan; SCHKERYANTZ, Jeffrey Michael; SHEN, Quanrong; VALLI, Matthew John; WETTERAU II, John Rowley; WODKA, Dariusz Stanislaw; XU, Yangping; (118 pag.)WO2018/34883; (2018); 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. 1427311-76-9, name is (S)-1-(4-Iodo-5-methoxy-2-nitrophenyl)-2,2-dimethylpropan-1-ol, A new synthetic method of this compound is introduced below., COA of Formula: C12H16INO4

DMAP (463 mg, 3.80 mmol) and MsCl (177 mu?, 2.28 mmol) were added to a solution of compound 4 (400 mg, 0.76 mmol) in anhydrous CH2CI2 (5.0 mL) at 0C under a nitrogen atmosphere. The reaction was stirred at 0C for 10 mins and at room temperature for another 3 hours. The reaction was then diluted with CH2CI2 (20 mL). The solution was applied on a short silica gel plug (2 x 3 cm) and was eluted quickly with a hexane/ethyl acetate/triethylamine solvent system (80 mL, volume ratio: 80/20/0.5). The eluent was concentrated in vacuo, and the residue was mixed with (5)-l-(4-iodo-5-methoxy-2- nitrophenyl)-2,2-dimethyl-l-propanol (500 mg, 1.37 mmol). The mixture was heated at 115C for 45 min under a nitrogen atmosphere, cooled to room temperature and dissolved in THF (10 mL). w-Bu4NF (526 mg, 1.67 mmol) was added and the mixture was stirred at room temperature for 12 hours and then concentrated in vacuo. The residue was dissolved in CH2CI2 (50 mL) and washed with brine (50 mL), and the aqueous phase was extracted with CH2CI2 (20 mL) two times. The combined organic phase was dried over Na2S04, concentrated in vacuo, and the residue was purified by silica gel chromatography to yield 6- chloro-9-(P-D-2′-deoxyribofuranosyl)-7-[(5)-l-(4-iodo-5-methoxy-2-nitrophenyl)-2,2- dimethyl-propyloxy]-methyl-7-deazapurine 51 (135 mg, 29% for three steps). 1H NMR (400 MHz, CDCl3): delta 8.56 (s, 1 H, H-2), 8.21 (s, 1 H, Ph-H), 7.34 (s, 1 H, H-8), 7.02 (s, 1 H, Ph- H), 6.35 (dd, 1 H, J= 6.0 and 8.8 Hz, Eta-Gamma), 5.20 (s, 1 H, Ph-CH), 4.76 (dd, 2 H, J= 12.4 and 36.4 Hz, 7-CH2), 4.74 (m, 1 H, H-3′), 4.13 (m, 1 H, H-4′), 3.96 (m, 1 H, H-5’a), 3.92 (s, 3 H, OCH3), 3.80 (m, 1 H, H-5’b), 2.85 (m, 1 H, H-2’a), 2.30 (m, 1 H, H-2’b), 0.83 (s, 9 H, C(CH3)3).

The synthetic route of 1427311-76-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LASERGEN, INC.; STUPI, Brian, Philip; LI, Hong; WU, Weidong; HERSH, Megan, N.; HERTZOG, David; MORRIS, Sidney, E.; METZKER, Michael, L.; WO2013/40257; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 52914-23-5, name is 2-(4-Iodophenyl)ethanol, 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 52914-23-5, Formula: C8H9IO

D. 2-(4-Iodophenyl)ethylchloride To a 500 mL round-bottomed flask equipped with dropping funnel, condenser and N2 inlet were added 307 g (124 mmol) 2-(4-iodophenyl)ethanol, 200 mL chloroform, and 10.0 mL (124 mmol) pyridine. A solution of 13.5 mL (186 mmol) thionyl chloride in 50 mL chloroform was added dropwise over 15 min, and the reaction then heated at reflux for 2 hr. The reaction was cooled, the solvent evaporated, and the residue taken up in ethyl acetate, washed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine, dried, and evaporated. The resulting oil was chromatographed on silica gel using 20% ethyl acetate in hexane as eluant to afford 32.6 g (99%) of the product as an oil. 1H-NMR (CDCl3, delta): 3.00 (t, J=7, 2H), 3.68 (t, J=7, 2H), 6.99 (m, 2H), 7.63 (m, 2H). 13C-NMR (CDCl3, delta): 38.6, 44.6, 92.3, 128.8, 130.9, 137.7.

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:
Patent; Pfizer Inc.; US6235747; (2001); B1;,
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. 52914-23-5, name is 2-(4-Iodophenyl)ethanol, A new synthetic method of this compound is introduced below., Safety of 2-(4-Iodophenyl)ethanol

EXAMPLE 19 n-Hexyl-p-Iodophenethyl Carbonate (m of Table I) p-Iodophenethyl alcohol was reacted with n-hexyl-chloroformate according to the carbonate synthesis of Procedure B. The isolated material gave an ir and nmr spectra in agreement with the proposed structure. The oil had a refractive index of ND25 = 1.5295. The mass spectrum (70 ev) parent ion was measured at m/e 376.0508, and calculated for C15 H21 IO3 at 376.0538. Analysis: calculated C15 H21 IO3: C, 47.91; H, 5.63; found C, 48.07; H, 5.66.

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; Lafayette Pharmacal, Inc.; US4022814; (1977); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 19231-06-2, 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. 19231-06-2 name is Bis(4-methoxyphenyl)iodonium bromide, 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.

107.2 g obtained in step (1) was added to the reactor.3,5-diiodo-L-tyrosine copper complex and 1000 ml of water,Then slowly add 1200ml of n-butanol to the inside.After the dropwise addition within 1 h, the reaction was dissolved. Then add 43.8g of diisopropylamineThereafter, 146 g of diphenyl methyl ether iodide bromide was further added. The reaction solution was heated to 90 C, and reacted at 90 C for 2 h, cooled to room temperature, and 280 ml of toluene was added. An additional 200 ml of 10% citric acid solution was added and stirred at room temperature for 2 h, filtered, washed with water and methyl isobutyl ketone. The obtained wet cake was further added with 400 ml of 10% citric acid solution and stirred for 1 h, filtered, and washed with 10% citric acid solution.Drying to give 2-amino-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)propionic acid (compound of formula III) 69.1 g,The yield was 59.3%, and it was used.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Bis(4-methoxyphenyl)iodonium bromide, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Tech University; Lu Dingqiang; Chen Li; Wang Xinxian; Ye Hui; (10 pag.)CN109810009; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 52914-23-5, 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. 52914-23-5 name is 2-(4-Iodophenyl)ethanol, 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.

3-[4-[2-(Benzyloxy)ethyl]phenyl]-5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]pyridine Into a 50-mL 3-necked round-bottom flask under N2 was placed a solution of 2-(4-iodophenyl)ethanol (470 mg, 1.90 mmol) in tetrahydrofuran (10 mL). Sodium hydride (91 mg, 3.8 mmol, 1.2 equiv.) was added at 0 C. The mixture was warmed to room temperature and stirred at room temperature for 2 h. Benzyl bromide (272 muL, 3.9 mmol, 1.2 equiv.) and tetra-n-butylammonium bromide (61 mg, 0.19 mmol, 0.10 equiv.) were added at room temperature. The resulting solution was stirred for 20 h at room temperature. The reaction was then quenched by the addition of 10 mL of aqueous NH4Cl. The solution was extracted with 3*60 mL of EtOAc, and the organic layers were combined and washed with 50 mL of brine. After evaporation, the residue was applied onto a silica gel column, and the product was eluted with EtOAc/petroleum ether 1:20 to furnish 600 mg (94%) of 1-[2-(benzyloxy)ethyl]-4-iodobenzene as a white solid. A solution/suspension of 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine (427 mg, 1.00 mmol), 1-[2-(benzyloxy)ethyl]-4-iodobenzene (338 mg, 1.00 mmol), CsF (304 mg, 2.00 mmol), Pd(PPh3)4 (58 mg, 0.05 mmol) and CuI (19 mg, 0.10 mmol) in anhydrous DMF (5 mL) was stirred at 50 C. for 5 h under N2. The reaction mixture was cooled and concentrated under vacuum. The residue was applied onto a silica gel column, and the product was eluted with EtOAc/petroleum ether/Et3N 3:6:0.5 as the eluent to give the title compound (280 mg, 59%) as light-yellow oil. 1H NMR (CDCl3, 300 MHz) delta 8.48 (s, 1H), 8.33 (d, J=2.1 Hz, 1H), 7.55 (d, J=8.1 Hz, 2H), 7.48 (s, 1H), 7.37-7.29 (m, 7H), 4.57 (s, 3H), 4.42 (s, 1H), 4.24 (dd, J=7.2, 3.0 Hz, 1H), 3.93 (t, J=7.2 Hz, 2H), 3.75 (t, J=7.2 Hz, 2H), 3.00 (t, J=7.2 Hz, 2H), 2.43-2.30 (m, 2H), 1.42 (s, 9H). LC-MS (ESI) m/z 475 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Iodophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; The Board of Trustees of the University of Illinois; PsychoGenics, Inc.; Chandrasekhar, Jayaraman; Kozikowski, Alan P.; Liu, Jianhua; Tueckmantel, Werner; Walker, Joel R.; Yuen, Po-wai; US2013/184313; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 206559-43-5, name is 5-Bromo-2-iodo-m-xylene, molecular formula is C8H8BrI, 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. HPLC of Formula: C8H8BrI

2.5 M n-Butyllithium, in tetrahydrofuran, (1.42 ml, 3.54 mmol, 1.1 equiv.) was added dropwise to a solution of bromobenzene (0.34 ml, 3.22 mmol, 1.0 equiv.) in dry tetrahydrofuran (18 ml), under nitrogen at -78 C. and the mixture stirred for 30 minutes. Zinc chloride (0.48 g, 3.54 mmol, 1.1 equiv.) was added and the mixture allowed to warm to room temperature while stirring for 2 hours. Palladium tetrakistriphenylphosphine (0.19 g, 0.16 mmol, 0.05 equiv.) and a solution of 5-bromo-2-iodo-1,3-dimethyl-benzene (1.00 g, 3.22 mmol, 1.0 equiv.) in tetrahydrofuran (2 ml) were added and the mixture stirred at room temperature for 16 hours. The tetrahydrofuran was evaporated under reduced pressure and the crude product purified by column chromatography (SiO2, heptane). The fractions were combined to afford 4-bromo-2,6-dimethylbiphenyl, 278 mg (33% yield) as a clear oil deltaH (400 MHz; d4-methanol) 7.28-7.39 (3H, m), 7.18 (2H, s), 7.03 (2H, d), 1.90 (6H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 206559-43-5, its application will become more common.

Reference:
Patent; Gubler, Marcel; Haap, Wolfgang; Hebeisen, Paul; Kitas, Eric A.; Kuhn, Bernd; Minder, Rudolf E.; Schott, Brigitte; Wessel, Hans P.; US2007/281979; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 249647-25-4, 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. 249647-25-4, name is 3-Bromo-4-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

Method 13: Synthesis of 5-(5-{2-r5-(3-bromo-4-iodophenyl)-l,2,4-oxadiazol-3-yll-3- meth lbutan-2-yl}pyridin-2-yl)pyrimidin-2-amine (Example 69)A suspension of R19 (163.3 mg, 0.50 mmol) and Iota,Gamma-carbonyldiimidazole (81.0 mg, 0.50 mmol) in THF (2.0 mL) is heated at 50C for 30 min. 1-8.4 (100.0 mg, 0.33 mmol) is added and the solution is heated under reflux for 3 hours. The mixture is cooled to room temperature and AcOH (0.2 mL) is added. The reaction mixture is stirred at 80C overnight. After cooling to room temperature, the mixture is poured into water and extracted with EtOAc. The organic layers are combined, dried over anhydrous Na2S04 and filtered. The solvent is removed under reduced pressure. Purification via silica gel column chromatography affords Example 69 (67.0 mg).

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-iodobenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John, D.; LIU, Weimin; LO, Ho Yin; LOKE, Pui Leng; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee, M.; WO2012/40137; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 914636-93-4, The chemical industry reduces the impact on the environment during synthesis 914636-93-4, name is 3-Fluoro-5-iodobenzaldehyde, I believe this compound will play a more active role in future production and life.

3-Fluoro-5-iodocinnamic Acid Methyl Ester 3-Fluoro-5-iodobenzaldehyde, monomethyl malonate, and a catalytic amount of pyrrolidine are heated in pyridine. After cooling, the solvent is distilled off in vacuo. 2N HCl and ethyl acetate are added to the residue, and the phases are separated. The organic layer is washed with brine and dried over Na2SO4. After evaporation, the residue is purified by CC on silica gel with EtOAc/hexane. Evaporation of appropriate fractions yields the title compound.

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, 3-Fluoro-5-iodobenzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Board of Trustees of the University of Illinois; PsychoGenics, Inc.; Chandrasekhar, Jayaraman; Kozikowski, Alan P.; Liu, Jianhua; Tueckmantel, Werner; Walker, Joel R.; Yuen, Po-wai; US2013/184313; (2013); 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. 59382-39-7, name is 1-Fluoro-4-iodo-2-(trifluoromethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C7H3F4I

Dissolve 1-fluoro-4-iodo-2-trifluoromethylbenzene (813 mg, 2. 8 mmol) in triethylamine (6 mL). Add 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (400 mg, 3. 0 mmol) followed by bis (triphenylphosphine) palladium (II) dichloride (0. 100 g, 0. 14 mmol) and copper (I) iodide (53 mg, 0. 28 mmol). Heat at 70 C for 16 h, concentrate, and purify using silica gel chromatography, eluting with 100 : 0 to 90 : 10 methylene chloride : ethyl acetate, to give the title compound as a pale yellow solid (820 mg, 99%). 1HNMR (300 MHz, CDCl3) 6 3. 89 (s, 3H), 7. 19-7. 26 (m, 1H), 7. 30-7. 31 (m, 1H), 7. 69- 7. 74 (m, 1H), 7. 79-7. 82 (m, 1H), 8. 30 (d, J = 2. 8 Hz, 1H), 8. 38 (d, J = 1. 3 Hz, 1H) ; MS (APCI) : m/z = 296 [M+H] +.

The synthetic route of 59382-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com