Category: 52570-33-9

Adding a certain compound to certain chemical reactions, such as: 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, 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 52570-33-9, category: iodides-buliding-blocks

To a solution of methyl 3-iodo-2-methylbenzoate (10.0 g, 36.2 mmol) in carbon tetrachloride (200 mL) was added BS (8.4 g, 47.1 mmol) and benzoyl peroxide (4.4 g, 18.1 mmol), the suspension was heated at 90 C overnight. The mixture was then cooled to RT and filtered. The filtrate was concentrated to give the crude product, which was purified by silica-gel column (light petro 100%) to give methyl 2-(bromomethyl)-3- iodobenzoate (9.8 g, 76%) as a yellow solid.

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

Reference:
Patent; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 52570-33-9, These common heterocyclic compound, 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, 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: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

The synthetic route of 52570-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
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. 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 3-iodo-2-methylbenzoate

0.2 mmol of potassium carbonate and 0.01 mmol of palladium acetate.0.02 mmol of triphenylphosphine, 0.2 mmol of methyl 2,3-dicarboxylate-7-oxanorbornadiene,2-fluoro-3-carboxylic acid methyl ester iodobenzene 0.1 mmol, hexamethyldisiloxane 0.15 mmol,1 mL of N,N-dimethylformamide was added to a 15 mL reaction tube.Nitrogen was repeatedly filled 3 times, placed in an oil bath at 100 C, and reacted for 12 h;After cooling to room temperature, the reaction solution was diluted with ethyl acetate and washed with water three times.The organic phase was dried over anhydrous Na2SO4, filtered and concentrated.Purified by column chromatography19.2mg of target product,The yield was 60%.

According to the analysis of related databases, 52570-33-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Huaqiao University; Cheng Guolin; Lv Weiwei; (13 pag.)CN109021003; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 52570-33-9,Some common heterocyclic compound, 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, molecular formula is C9H9IO2, 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.

Under a nitrogen atmosphere, 2-amino-3-bromo-5- methylpyridine (2.00 g, 10.69 mmol) , methyl 3-iodo-2- methylbenzoate (2.95 g, 10.69 mmol) , copper (I) iodide (204 mg, 0.11 mmol), ethanol amine (131 mg, 0.22 mmol), potassium carbonate (2.22 g, 16.04 mmol), and anisole (30 ml) were mixed, and the mixture was stirred at room temperature for 10 minutes. The mixture was heated and stirred at 130C for 8 hours. The reaction solution was cooled to room temperature, and water (30 ml) was added thereto. The mixture was concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate (50 ml), activated carbon Shirasagi A was added, and the mixture was filtered. Water (20 ml) was added to the filtrate. The organic layer was separated and washed with water (20 ml) . The organic layer was concentrated. The concentrate was subjected to silica gel column chromatography (silica gel 20 g, eluent: ethyl acetate :n-hexane = 1:20), and the effective fraction was concentrated. Ethyl acetate (0.2 ml) and n-hexane (5 ml) were added to the residue, and the mixture was stirred at room temperature for 30 minutes. Next, the crystals were collected by filtration, and dried at 50C under reduced pressure, to yield the title compound (1.13 g) . (HPLC area%: 83.4% (methyl 3- [ (3-iodo-5-methylpyridin-2- yl) amino] -2-methylbenzoate: 16.1%)) .

The synthetic route of 52570-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/16184; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 52570-33-9, 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. 52570-33-9 name is Methyl 3-iodo-2-methylbenzoate, 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.

Process using Pd Catalyst Under a nitrogen atmosphere, palladium acetate (223 mg, 0.99 mmol) , 4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene (Xantphos) (575 mg, 0.99 mmol) and toluene (62 ml) were mixed, and the mixture was stirred at room temperature for 15 minutes. To this solution, 2-amino-3-bromo-5-methylpyridine (6.20 g, 33.15 mmol), methyl 3-iodo-2-methylbenzoate (9.15 g, 33.15 mmol) and cesium carbonate (15.12 g, 46.41 mmol) were added. The mixture was stirred at an internal temperature of 100 to 105C for 7 hours. The reaction solution was cooled to room temperature, and water (50 ml) and toluene (50 ml) were added thereto. The organic layer was separated and washed sequentially with water (40 ml) and 10% brine (40 ml) . Silica gel (6 g) was added to the organic layer, the mixture was filtered, and the filtrate was concentrated under reduced pressure. Ethyl acetate (0.5 ml) and n-hexane (6 ml) were added to the concentrate, and the mixture was stirred at room temperature for 30 minutes. The crystals were collected by filtration, washed with ethyl acetate/n-hexane (1/12, 5 ml), and dried under reduced pressure at 40C, to yield the title compound (4.81 g) (yield 43.3%). 1H-NMR (CDCl3, TMS, 300 MHz) delta (ppm) : 2.23 (3H, s) , 2.52 (3H, s), 3.91 (3H, s), 6.78 (IH, brs) , 7.27 (IH, t, J = 8.0 Hz), 7.57-7.62 (2H, m) , 7.95 (IH, d, J = 1.1 Hz), 8.10 (IH, dd, J = 1.0 Hz, 8.1 Hz) .High resolution mass spectrometry Theoretical value: 334.0317 [M+] Measured value: 334.0313 [M+]Melting point: 63.9 to 64.7C

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

Reference of 52570-33-9, These common heterocyclic compound, 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, 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.

To a solution of methyl 3-iodo-2-methylbenzoate (5.20 g, 18.8 mmol) in CCI4 (90 mL) at RT was added N-bromosuccinimide (NBS) (4.02 g, 22.6 mmol) then the reaction flask was purged with N2. After the mixture was stirred at 85 C for 5 m, 2,2?-azobis(2- methylpropionitrile) (AIBN) (1.62 g, 9.42 mmol) was added. The mixture was stirred overnight at 85 C then concentrated. The residue was diluted with H2O and extracted with EtOAc. The organic phase was dried over Na2S04, filtered, and concentrated to give the crude product, which was purified using silica gel eluting with EtOAc in petroleum ether from 0% to 1% to afford methyl 2-(bromomethyl)-3-iodobenzoate (2.64 g, 40% yield) as a solid.

Statistics shows that Methyl 3-iodo-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 52570-33-9.

Reference of 52570-33-9, These common heterocyclic compound, 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, 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.

[0470] To a solution of methyl 3-iodo-2-methylbenzoate (15 g, 54.35 mmol) in N,N-dimethylacetamide (200 mL) at rt was added K4[Fe(CN)6].3H2O (5.74 g, 13.59 mmol) and sodium carbonate (5.76 g, 54.35 mmol), followed by palladium acetate (1.5 g) added. The suspension was evacuated and replaced with nitrogen, then heated to 120C for 10 hrs. The reaction mixture was cooled to rt, filtered, and the filtrate was diluted with water (100 mL), and extracted with EA (200 mL) twice. The combined organic layers were washed with water, brine, dried over sodium sulfate, filtered and concentrated providing the crude product, which was purified by column chromatography on silica-gel elution with petroleum ether:EA (from 50/1 to 30/1) providing methyl 3-cyano-2-methylbenzoate (4.6 g, 48.4% yield) as a white solid. MS (ESI) m/z 175.9 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.08 (d, J = 7.6 Hz, 1 H), 7.76 (d, J = 8.0 Hz, 1 H), 7.36 (t, J = 7.6 Hz, 1 H), 3.93 (s, 3 H), 2.80 (s, 3 H).

The synthetic route of 52570-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTHERYX, INC.; CHAN, Kyle, W.H.; FUNG, Leah; SULLIVAN, Robert; ERDMAN, Paul, E.; MERCURIO, Frank; (225 pag.)WO2017/201069; (2017); 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 52570-33-9 as follows. Recommanded Product: 52570-33-9

b. 3-Iodo-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid methyl ester[0236] A mixture of 3-iodo-2-methyl-benzoic acid methyl ester (75 mmol, 20.7 g), N- bromosuccinimide (76.6 mmol, 13.8 g), benzoyl peroxide (890 mg), and CCl4 (300 mL) was refluxed with stirring for 15 h. After cooling to ambient temperature the mixture was filtered and the filtrate was concentrated in vacuo to give the title compound as a tan oil. The oil (26.3 g) was dissolved in dry DMF (75 mL). NaI (22.4 g), K2CO3 (20.5 g), and (toluene-4- sulfonylamino)-acetic acid methyl ester (19 g) were added and the mixture was stirred at ambient temperature for 24 h before it was poured into water (900 mL). The mixture was extracted with ethyl acetate (2×250 mL). The combined organic phases were washed with a solution of sodium meta-bisulfte (20 g) in water (300 mL) and water (2×300 mL) before they were dried over MgSO4 and concentrated in vacuo to give the title compound as a dark gum (38.1 g). The crude product was used in the next step without further purification; MS-(+)-ion: M+23 = 539.9.

According to the analysis of related databases, 52570-33-9, the application of this compound in the production field has become more and more popular.

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

Adding a certain compound to certain chemical reactions, such as: 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, 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 52570-33-9, Product Details of 52570-33-9

0.3 mmol of sodium carbonate, 0.1 mmol of diphenylacetylene, and 0.005 mmol of palladium acetate.Bis(2-diphenylphosphinophenyl)ether 0.005 mmol, hexamethyldisilane 0.15 mmol,0.15 mmol of methyl 3-iodo-2-methylbenzoate and 1 mL of N,N-dimethylformamide were added to a 15 mL reaction tube.Nitrogen was repeatedly filled 10 times, placed in an oil bath at 100 C, and reacted for 24 hours;Cooled to room temperature, the reaction was diluted with ethyl acetate, washed with water three times, the organic phase dried over anhydrous Na2SO4, filtered, and concentratedPurification by thin layer chromatography to give 24.6mg of the desired product, yield 52%.

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; Huaqiao University; Cheng Guolin; Lv Weiwei; (20 pag.)CN109879713; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com