Month: May 2021

Synthetic Route of 180624-10-6, A common heterocyclic compound, 180624-10-6, name is Methyl 4-amino-3-iodo-5-methoxybenzoate, molecular formula is C9H10INO3, 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.

Palladium acetate (73 mg, 0.22 mmol) was added to a solution of 3-iodo-4-amino-5-methoxybenzoate (1.0 g, 3.25 mmol), methyl acrylate (0.32 mL, 3.6 mmol), triphenylphosphine (0.17 g, 0.65 mmol), and triethylamine (0.9 mL, 6.5 mmol) in CH3CN (10 mL). The mixture was flushed with Ar and heated at 80 C. in a sealed tube for 90 mins. The mixture was diluted with EA, and washed with 1N HCl and brine. The organic layers were dried and concentrated. Crude 11-1 was chromatographed (hexane:EA) to give 11-1 (0.52 g, 57%). LC/MS: 280.05 [M+H]+.

The synthetic route of 180624-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alios BioPharma, Inc.; Wang, Guangyi; Beigelman, Leonid; Truong, Anh; Stein, Karin Ann; (234 pag.)US2016/244460; (2016); 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. 180624-08-2, name is 4-Bromo-2-iodo-6-nitroaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H4BrIN2O2

4-bromo-2-iodo-6-nitroaniline (150 mg, 0.44 mmol) and 3,5-Dimethylisoxazole-4-boronic acid pinacol ester (390 g, 1.75 mmol) was added to a solvent mixture of 1,2-dimethoxyethane (2 ml) and water (1 ml). To the above mixture were added PEPPSI-Ipr (30 mg, 0.04 mmol) and Cs2CO3 (0.86 g, 2.64 mmol). The reaction mixture was heated at 120 C. in microwave reactor for 2 hs. The reaction mixture was then diluted with EtOAc (100 ml), washed with bring (50 ml, 2 times). The organic solvent was evaporated and the residue was dissolved in DCM and purified with combi-flash column chromatography (product came out at 25% MeOH/DCM) to afford 2,4-bis(3,5-dimethylisoxazol-4-yl)-6-nitroaniline. C16H16N4O4. 329.2 (M+1)

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 180624-08-2.

Reference:
Patent; Gilead Sciences, Inc.; Aktoudianakis, Evangelos; Chin, Gregory; Corkey, Britton Kenneth; Du, Jinfa; Elbel, Kristyna; Jiang, Robert H.; Kobayashi, Tetsuya; Lee, Rick; Martinez, Ruben; Metobo, Samuel E.; Mish, Michael; Munoz, Manuel; Shevick, Sophie; Sperandio, David; Yang, Hai; Zablocki, Jeff; US2014/336190; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 51738-07-9, The chemical industry reduces the impact on the environment during synthesis 51738-07-9, name is 2-Chloro-6-iodobenzaldehyde, I believe this compound will play a more active role in future production and life.

The mixture of TsNHNH2 (3.16 mmol, 1.0 eq) and DME (6.0 mL) was stirred and heated to 60 Cuntil a clear solution was obtained. The mixture was cooled to 25 C, and then 2-chloro-6-iodobenzaldehyde (3.2 mmol, 1 eq) dissolved in DME (2 mL) was added dropwise to the mixtureunder stirring. After approximately 1 h, CuI (0.32 mmol, 10 mol %), diethyl H-phosphonate (2.88mmol, 1.0 eq) and Cs2CO3 (4.74 mmol, 1.5 eq) were added sequentially to the reaction mixture at25 C. The mixture was then heated under stirring at 80 C for 3 h. When the reaction wascomplete (TLC control), the mixture was allowed to cool to 25 C. It was then filtered through ashort plug of SiO2 (AcOEt). The solvent was evaporated in vacuum. The residue was purified bysilica gel column chromatography (40 % EtOAc/petroleum ether) to afford an oil, 0.40 g, (35%).

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, 2-Chloro-6-iodobenzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Roehrig, Ute F.; Majjigapu, Somi Reddy; Caldelari, Daniela; Dilek, Nahzli; Reichenbach, Patrick; Ascencao, Kelly; Irving, Melita; Coukos, George; Vogel, Pierre; Zoete, Vincent; Michielin, Olivier; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4330 – 4333;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

133232-56-1, name is 3-Iodo-2-methylbenzoic acid, 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. Recommanded Product: 3-Iodo-2-methylbenzoic acid

(W02006117669 (Al)): To a solution of 3-iodo-2-methylbenzoic acid (5.00 g, l9.08mmol) in MeOH (20 mL) was added dropwise a solution of SOCh (4.16 mL, 57.24 mmol) in MeOH (10 mL) at 0 C. The mixture was heated to reflux for 3 h. The mixture was concentrated and the residue obtained was purified using S1O2 chromatography eluting with EtOAc in hexanes (0-15% EtOAc, gradient elution) to provide the title compound 5 as a brown oil (4.00 g, 75%). 1H NMR (500 MHz, CDC13) d 8.00 (dd, J = 1.3, 7.9 Hz, 1H), 7.76 (dd, J = 1.3, 7.7 Hz, 1H), 6.95 (td, J = 0.7, 7.8 Hz, 1H), 3.93 (s, 3H), 2.69 (s, 3H). HPLC-MS (ESI+): m/z 276.9 [100%, (M+H)+], 761.3 [72%, (M+Na)+]

The synthetic route of 133232-56-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; BURNETTE, Pearlie; LAWRENCE, Nicholas J.; LAWRENCE, Harshani; (0 pag.)WO2020/14489; (2020); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 345226-19-9, 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. 345226-19-9, name is 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

A stirred mixture of 4-(hydroxymethyl)phenylboronic acid (34) (308 mg, 2.03 mmol) and Pd(dppf)Cl2 (191 mg, 0.261 mmol) in toluene (22 mL) and EtOH (11 mL) was degassed for 8 min (vacuum pump) and then N2 was added. An aqueous solution of 2M Na2CO3 (4.4 mL, 8.8 mmol) was added by syringe and the stirred mixture was again degassed for 8 min, and then N2 was added. 2-Chloro-l-iodo-4-(trifluoromethoxy)benzene (35) (585 mg, 1.81 mmol) was added by syringe and the resulting mixture was stirred at 88 0C for 60 min. The cooled mixture was then diluted with aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (5x 100 mL). The extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-50% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 50% CH2Cl2/petroleum ether gave 2′-chloro-4′-(trifluoromethoxy)[l,r-biphenyl]-4-yl]methanol (37) (537 mg, 98%) as a white solid: mp (pentane) 38-39 C; 1H NMR (CDCl3) delta 7.46 (br d, J = 8.2 Hz, 2 H), 7.42 (dt, J = 8.3, 2.0 Hz, 2 H), 7.37 (br s, 1 H), 7.36 (d, J = 8.5 Hz, 1 H), 7.19 (m,I H), 4.77 (d, J = 5.9 Hz, 2 H), 1.70 (t, J = 5.9 Hz, 1 H); HREIMS calcd for C14H10ClF3O2 mlz (M+) 304.0292, 302.0321 , found 304.0294, 302.0317.

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

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; DENNY, William, Alexander; THOMPSON, Andrew, M.; BLASER, Adrian; MA, Zhenkun; PALMER, Brian, Desmond; SUTHERLAND, Hamish, Scott; KMENTOVA, Iveta; WO2011/14774; (2011); 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. 1031929-20-0, name is 4-Fluoro-2-iodobenzonitrile, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

ntermediate 87: 4-Fluoro-2-(pyrimidin-2-yl)benzoic acid.Step A: 2-lodo-4-fluorobenzonitrile (2.54 g, 10.3 mmol) and 2- tributylstannane pyrimidine (3.69 g, 10.0 mmol) were dissolved indomethoxyethane (18 mL) and treated with tetrakistriphenylphosphine palladium (0) (578 mg, 0.5 mmol) and copper (I) iodide (95 mg, 0.5 mmol). The reaction was then heated to 160 C for 90 minutes in the microwave. The reaction was cooled, concentrated under reduced pressure. Chromatography (20-100% EA in hexanes) gave the desired product. 1 H NMR (400 MHz, CDCIs): 8.93 (d, J = 4.9 Hz, 2H), 8.14 (dd, J = 9.6, 2.7 Hz, 1 H), 7.86 (dd, J = 8.6, 5.3 Hz, 1 H), 7.36 (t, J = 4.9 Hz, 1 H), 7.32 – 7.23 (m, 1 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; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 133232-56-1,Some common heterocyclic compound, 133232-56-1, name is 3-Iodo-2-methylbenzoic acid, molecular formula is C8H7IO2, 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.

Example 19{fl-Cyano-4-hydroxy-8-(4-methoxy-phenoxy)-isoquinoline-3-carbonyll-amino}-acetic acid a. 3-Iodo-2-methyl-benzoic acid methyl ester[0235] A mixture of 3-iodo-2-methyl-benzoic acid (90 mmol, 23.6 g), methanol (250 mL), and concentrated sulfuric acid (13 mL) was re fluxed with stirring for 40 h before it was concentrated in vacuo. The residue was dissolved in ethyl acetate and the mixture was neutralized by adding small portions of a saturated aqueous NaHCOs solution with stirring. The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a yellowish oil (24.3 g); 1H NMR (CDCl3, 200 MHz): delta = 7.96 (d, 1 H), 7.71 (d, 1 H), 6.91 (t, 1 H), 3.89 (s, 3 H), 2.66 (s, 3 H).

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

Reference:
Patent; FIBROGEN, INC.; WO2007/90068; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 773136-66-6, 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 773136-66-6 as follows.

Add NaH (3.71 g, 92.8 mmol, 60.0% purity, 1.3e q) to dry THF (131.0 mL).Compound 2 (21.0 g, 71.4 mmol, 1 eq) and 1-vinylpyrrolidin-2-one (8.49 g, 76.4 mm ol, 8.17 mL, 1.07 eq).The mixture was stirred at 80 C for 3 hours.It was then cooled to room temperature.Then 10% HCl solution (30 mL) was slowly added and stirred at 100 C for 10 hours.The progress of the reaction was detected by TLC (P etroleum ether/Ethyl acetate = 4/1, Rf = 0.68).When the reaction is over,In the condition of an ice bath,Gradually add 1M NaOH solution,The pH of the reaction solution was adjusted to 8.0.Further extraction with DCM (50.0 mL x 2),And by column chromatography (SiO2,Petroleum ether/Ethyl acetate=8/1to 5/1),Obtained white compound 3 (1.60 g, 5.53 mmol,7.75% yield).Figure 4 shows the results of TLC chromatography for this reaction.The NMR data for Compound 3 is:

According to the analysis of related databases, 773136-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Health Medical School; Tang Dewei; Huang Gang; Huang Chen; Wu Xingyu; Yu Meicen; Li Yanjiao; (18 pag.)CN109942582; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 954815-11-3, name is 4-Iodo-2-(trifluoromethyl)benzoic acid, 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 954815-11-3, SDS of cas: 954815-11-3

Under argon, first 3.34 g (7.90 mmol) of N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-acrylamide from Example 2, Stage 1, and then 2.49 g (7.90 mmol) of 4-iodo-2-(trifluoromethyl)benzoic acid (commercially available, CAS Registry Number: 954815-11-3), 0.206 g (7.90 mmol) of triphenylphosphine, 88.4 mg (0.39 mmol) of palladium(II) acetate and 13.5 g (133 mmol) of triethylamine were initially charged in 67 ml of N,N-dimethylformamide, and the reaction mixture was stirred at 100 C. for 5 hours. After addition of water, the solution was extracted with ethyl acetate, and then the organic phase was washed three times with saturated sodium chloride solution and dried over sodium sulphate. The solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel with ethyl acetate.Yield: 2.57 g (60% of theory).1H NMR (400 MHz, d6-DMSO) delta=6.10 (m, 1H), 6.93 (d, 1H), 7.6 (m, 1H), 7.69 (m, 1H), 7.75 (m, 2H), 7.85 (m, 1H), 7.95 (m, 1H), 7.99 (m, 1H), 9.38 (d, 1H).HPLC-MS: logP=3.29; mass (m/z): 486.0 (M+H)+.In analogy to the method described in Synthesis Example 2, Stage 2, the following compounds of the general formula (I-5) were also obtained:

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; Bayer CropScience AG; US2011/105532; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 52107-68-3, These common heterocyclic compound, 52107-68-3, name is 5-Iodo-2-methylbenzonitrile, 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.

A stirred slurry of sodium hydride (60% dispersion in mineral oil, 480 mg, 12.0 mmol) in DME (3.0 mL)was refluxed. 5-iodo-2-methylbenzonitrile (729 mg, 3.00 mmol), methyl benzoate (544 mg, 4.00 mmol),and DME (3.0 mL) were added to the slurry. After a catalytic amount of MeOH was added, the mixture was refluxed for 7 h. The mixture was cooled to 0C. water (10 mL) was added to quench the reactionand then 2 M HCl (10 mL) was added. The resulting mixture was diluted with EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, and filtered. The solvents were evaporated in vacuo. The crude product was purified by recrystallization from ethanol to give 5-iodo-2-(2-oxo-2-phenylethyl)benzonitrile (5g)(635 mg, 61%). Yellow white solid. Mp 134-136C. 1H NMR (400 MHz, CDCl3): delta = 7.98-8.04 (m, 3H),7.87-7.89 (m, 1H), 7.60-7.64 (m, 1H), 7.49-7.53 (m, 2H), 7.10-7.13 (m, 1H), 4.49 (s, 2H). 13C NMR (100MHz, CDCl3): delta = 194.7, 141.8, 140.8, 138.1, 136.0, 133.8, 132.6, 128.8, 128.3, 116.3, 115.6, 91.7, 43.2.IR (KBr): 3097, 3056, 3033, 2951, 2884, 2230, 1688, 1594, 1479, 1448, 1416, 1385, 1332, 1204, 1110,988, 906, 868, 837, 806, 752 cm-1. HRMS (EI): Calcd for C15H10INO 346.9807 (M)+, found 346.9820.

Statistics shows that 5-Iodo-2-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 52107-68-3.

Reference:
Article; Yashiro, Kai; Sakata, Keito; Hachiya, Iwao; Shimizu, Makoto; Heterocycles; vol. 92; 11; (2016); p. 2032 – 2046;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com