Category: 618-91-7

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 618-91-7 as follows. HPLC of Formula: C8H7IO2

To the mixture of methyl 3-iodobenzoate (157 mg, 0.60 mmol), potassium carbonate (166 mg, 1.20 mmol), cupper(I) iodide (14 mg, 0.07 mmol) and PdCi2(Ph3P)2 (21 mg, 0.03 mmol) in tetrahydrofuran (2 mL) was added tert-butyl propiolate (330 muL, 2.40 mmol) at room temperature. After stirred for 20 h at 60C, the mixture was evaporated to dryness. The residue was chromatographed on a silica gel (EtOAc:hexanes 0: 1~1 : 10) to give the title compound 9-1 (155 mg, 99% yield) as a light brown oil. 1H NMR (300 MHz, CDCl3) delta 8.25 (t, J= 1.4, 1H), 8.16 – 8.05 (m, 1H), 7.80 – 7.68 (m, 1H), 7.46 (t, J= 7.8, 1H), 3.93 (s, 3H), 1.55 (s, 9H).

According to the analysis of related databases, 618-91-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE BROAD INSTITUTE, INC.; MASSACHUSETTS GENERAL HOSPITAL; HUNG, Deborah; STANLEY, Sarah; KAWATE, Tomohiko; IWASE, Noriakie; SHIMIZU, Motohisa; WO2013/49567; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 618-91-7,Some common heterocyclic compound, 618-91-7, name is Methyl 3-iodobenzoate, 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.

To a solution of methyl 3-iodobenzoate (4.5 g, 17.2 mmol) in DMSO (30 mL) was added 3-azetidin-3-ol hydrogen chloride salt (1.3 g, 11.8 mmol), Cs2CO3 (9.5 g, 29.2 mmol), CuI (446 mg, 2.3 mmol) and L-proline (540 mg, 4.7 mmol) and then the mixture was heated at 90 C. for 18 h under argon atmosphere. The solution was diluted with EA and water and the organic layer was washed with brine three times, concentrated under reduced pressure and purified by CC (PE/EA=2:1) to give compound 3a (1.6 g, 66%) as a yellow solid

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

Reference:
Patent; PHENEX PHARMACEUTICALS AG; Kinzel, Olaf; Steeneck, Christoph; Kremoser, Claus; US2014/221659; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 618-91-7, 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. 618-91-7, name is Methyl 3-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

3(ii) 3-Trimethylstannyl-benzoic acid methyl ester (3)Microwave 2 3To a mixture of methyl 3-iodobenzoate 200 mg, 0.76 mmol), and hexamethylditin (643 mul, 3.1 mmol) in toluene (8 ml) was added tetrakis (triphenylphosphine) palladium (0) (180 mg, 0.155 mmol (10 mol %). The reaction tube was flushed with argon, capped and heated in a microwave at 120C for 15 minutes. After cooling, TLC (ethyl acetate/hexane, 1 :1 ) showed complete conversion to product. Then the black suspension was filtered (filter paper) and the resulting dark coloured solution was evaporated to dryness. The residue was dissolved in ethyl acetate (15 ml) and extracted with water (6×10 ml).Then the organic phase was dried (MgSO4) filtered and evaporated under reduced pressure to afford the crude product as a dark oil (463 mg) which was purified by flash chromatography (Ethyl acetate: hexane, 1 :1 ) to afford a slightly yellow oil. Yield: 344 mg (74%).NB: Microwave irradiation was carried out in a Personal Chemistry Emrys synthesizer.1H NMR (500 MHz, CDCI3, £0.32 (s, 9H, Sn(CH3)3, 3.95(s, 3H, CH3), 7.40 (t, 1 H), 7.69 (d, 1 H), 8.0 (d 1 H), 8.20 (s, 1 H)

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

Reference:
Patent; GE HEALTHCARE LIMITED; AVORY, Michelle; BROWN, Jane; IVESON, Peter Brian; WO2010/86398; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

618-91-7, name is Methyl 3-iodobenzoate, 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. Safety of Methyl 3-iodobenzoate

General procedure: In a 10 mL glass screw cap tube capped with a rubber septum, palladium acetate Pd(OAc)2, (5 mg, 0.023 mmol), 1,3-bis(diphenylphosphino)propane dppp, (9 mg, 0.023 mmol) were introduced under argon atmosphere. Then, 3 mL of freshly distilled toluene) were added under argon. The mixture was stirred for 10 min to allow formation of the catalyst. Then securinine 1 (100 mg, 0.46 mmol), potassium carbonate (K2CO3, 127 mg, 0.92 mmol) and the desired iodoarene (0.92 mmol) were added. The septum was replaced by a screw cap, and the mixture was stirred at 130 C, in an oil bath. After 24 h stirring, the reaction mixture was brought to room temperature and diluted with ethyl acetate (5 mL). The reaction mixture was filtered through a pad of Celite eluting with AcOEt (20 mL). The organic layer was extracted with a saturated aqueous solution of sodium hydrogen carbonate (10 mL) and brine (10 mL). The organic layer was then dried over anhydrous magnesium sulfate, filtered and concentrated to dryness. Purification by flash column chromatography on silica gel (pentane-ethyl acetate) affords the desired coupling product. 4.1.2.1.14 Methyl 3-((6S,11aR,11bS)-2-oxo-2,6,9,10,11,11a-hexahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-5-yl)benzoate(2n) Yield: 67%. Orange solid; m.p. 54-56 C; Rf 0.32 (petroleum ether-AcOEt, 70:30); [alpha]D20 – 505 (c = 0.11, CHCl3); 1H NMR (300 MHz, CDCl3): delta = 8.18 (s, 1H), 8.02 (d, J = 7.8 Hz, 1H), 7.69 (d, J = 7.8 Hz, 1H), 7.48 (dd, J = 7.8 Hz, 1H), 6.86 (d, J = 1.3 Hz, 1H), 5.61 (s, 1H), 4.38 (d, J = 4.2 Hz, 1H), 3.92 (s, 3H), 2.92-2.86 (m, 1H), 2.64 (dd, J = 9.3, 4.2 Hz, 1H), 2.33-2.18 (m, 2H), 1.91-1.82 (m, 2H), 1.68-1.47 (m, 4H), 1.26-1.14 (m, 1H); 13C NMR (75 MHz, CDCl3): delta = 173.6, 169.9, 166.3, 149.1, 138.7, 130.9, 130.4, 130.2, 129.0, 127.4, 116.2, 105.2, 89.0, 63.0, 61.6, 52.3, 48.8, 41.9, 27.4, 25.8, 24.1. MS (CI, NH3): m/z = 352 [M+ + H]. HRMS calcd for C21H21N O4H [M+ + H]: 352.15433; found: 352.15386, error = 1.3 ppm.

The synthetic route of 618-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Perez, Marc; Ayad, Tahar; Maillos, Philippe; Poughon, Valerie; Fahy, Jacques; Ratovelomanana-Vidal, Virginie; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 287 – 293;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 618-91-7, name is Methyl 3-iodobenzoate, 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 618-91-7, Quality Control of Methyl 3-iodobenzoate

General procedure: An oven-dried Schlenk tuble equipped with a magnetic stirring bar was charged with MCM-41-N,N-Pd(OAc)2 (49 mg, 0.02 mmol Pd), aryl iodide (3.2 mmol), triarylbismuth (1.0 mmol), and K2CO3 (4.0 mmol) followed by anhydrous NMP (3 mL) under Ar. The reaction mixture was stirred in an oil bath at 110 C for 5-24 h. The reaction mixture was cooled to room temperature and filtered. The MCM-41-N,N-Pd(OAc)2 complex was washed with distilled water (2×5 mL), NMP (2×5 mL) and Et2O (2×5 mL) and reused in the next run. The filtrate was quenched with water, and extracted with ethyl acetate (2×30 mL). The combined ethyl acetate extract was washed with dilute hydrochloric acid (10 mL), saturated sodium bicarbonate solution (10 mL), brine (2×10 mL), and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica gel.

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, Methyl 3-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Caifeng; Yin, Lin; Huang, Bin; Liu, Haiyi; Cai, Mingzhong; Tetrahedron; vol. 72; 17; (2016); p. 2065 – 2071;,
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. 618-91-7, name is Methyl 3-iodobenzoate, A new synthetic method of this compound is introduced below., COA of Formula: C8H7IO2

General procedure: Under an inert nitrogen atmosphere, silver triflate (386 mg,1.5 mmol) was transferred to a Teflon sealed thick-walled 50 ml glass reaction vessel equipped with a stir bar, followed by aryl iodide (1.0 mmol), arene (2.0 mmol), DCE (4 ml) and then a freshly prepared stock solution of [Pd(allyl)Cl]2 (0.2 mg, 5 × 10-4 mmol). The vessel was closed, removed from the glovebox, evacuated and backfilled with carbon monoxide three times, and finally pressurized with 4 atm carbon monoxide. After heating at 100 C for 24 h with stirring, the reaction was cooled to room temperature and carbon monoxide was released. The reaction mixture was filtered through Celite, eluting with dichloromethane. Saturated NaHCO3 was added and the aqueous layer was extracted with dichloromethane. The combined organic layers were concentrated in vacuo and the residue was purified by column chromatography (silica gel, gradient hexane/ethyl acetate 0 to 20%) to afford the pure ketone product.

The synthetic route of 618-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kinney, R. Garrison; Tjutrins, Jevgenijs; Torres, Gerardo M.; Liu, Nina Jiabao; Kulkarni, Omkar; Arndtsen, Bruce A.; Nature Chemistry; vol. 10; 2; (2018); p. 193 – 199;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

618-91-7, name is Methyl 3-iodobenzoate, 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: 618-91-7

General procedure: A mixture of substituted iodobenzenes (1a-1i, 15 mmol), (5-formylfuran-2-yl)boronic acid(2, 15 mmol), bis(triphenylphosphine)palladium(II) chloride (Pd(Pph3)2Cl2, 0.6 mmol) and sodium carbonate (Na2CO3, 30 mmol) in MeCN/H2O (10 mL /10 mL) was stirred for 1 h at 60 C. Upon completion of the reaction as determined by TLC, MeCN was removed by a rotary evaporator under reduced pressure, and the residue was acidated with 1M HCl solution (pH 7) and filtered. Next,the ltrate was partitioned between water (60 mL) and ethyl acetate (3 x 50 mL). The organic layer wasdried over magnesium sulfate anhydrous (MgSO4), filtered and concentrated in vacuo. The crude products were purified by column chromatography with appropriate eluents to give the coupling products 3a-3i, in 80-86% yields.

The synthetic route of 618-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Lijiao; Li, Chao; Chen, Wei; Song, Chen; Zhang, Xing; Yang, Fan; Wang, Chen; Zhang, Yuanyuan; Qian, Shan; Wang, Zhouyu; Yang, Lingling; Molecules; vol. 24; 15; (2019);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 618-91-7,Some common heterocyclic compound, 618-91-7, name is Methyl 3-iodobenzoate, 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.

3-((E)-2-benzyloxycarbonyl-2-tert-butoxycarbonylamino- vinyl)-benzoic acid methyl ester: To 84A (10 g, 0.036 mol) dissolved in DMF (100 mL) were added methyl 3-iodobenzoate (9.5 g, 0.036 mol), palladium acetate (0.25 g, 1.08 mmol), tetrabutylammonium chloride (H g, 0.039 mol), and triethyl amine (15 mL, 0.108 mol). The mixture was flushed with nitrogen for 1 h, then heated at 85 0C overnight. The reaction mixture was diluted with brine and extracted with ethyl acetate. The organic layer was washed with brine and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 10% ethyl acetate in petroleum ether to give 84B (10 g, 67.5%).

The synthetic route of 618-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/70826; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 618-91-7, The chemical industry reduces the impact on the environment during synthesis 618-91-7, name is Methyl 3-iodobenzoate, I believe this compound will play a more active role in future production and life.

Substrate Compound 1 was arylated following the general arylation procedure A. Analysis of crude reaction mixture by XH NMR showed a > 20:1 ratio of mono- and diarylated products. After purification by column chromatography using hexane/EtOAc (5/1) as the eluent, Compound 21 was obtained as a white solid (50.0 mg, 88%). JH NMR (400 MHz, CDC13) delta 8.58 (br s, 1H) , 7.85-7.77 (m, 4H) , 7.75-7.70 (m, 2H) , 7.41-7.38 (m, 1H) , 7.30-7.26 (m, 1H) , 5.34 (dd, Ji = 6.0 Hz, J2 = 10.4 Hz, 1H), 3.80 (s, 3H) , 3.69 (ABqd, Jx = 6.2 Hz, J2 = 14.3 Hz, 1H) , 3.63 (ABqd, Ji = 10.4 Hz, J2 = 14.3 Hz, 1H) ; 13C NMR (100 MHz, CDC13) delta 167.9, 166.6, 166.4, 136.0, 134.7, 133.5, 131.0, 130.5, 130.0, 128.9, 128.6, 123.9, 56.2, 52.1, 34.9; HRMS (ESI-TOF) Calcd for C26Hi6F7N205 [M+H]+: 569.0942; found: 569.0941. Large scale reaction: Substrate Compound 1 (10 mmol, 4.34 g) , Pd(TFA)2 (1.0 mmol, 0.33 g) , and Ag2C03 (15 mmol, 4.14 g) were weighed in air and placed in a round-bottom flask (100 mL) with a magnetic stir bar. Methyl 3-iodobenzoate (15 mmol, 3.93 g) , 2-picoline (2.0 mmol, 0.19 g) , TFA (2.0 mmol, 0.23 g) , and DCE (35 mL) were added. The pressure vessel was sealed. The reaction mixture was first stirred at room temperature for 10 minuters and then heated to 100 C. Upon completion, the reaction mixture was purified by a silica gel-packed flash chromatography column, and Compound 21 was obtained in 78% yield (4.43 g) .

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, Methyl 3-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; YU, Jin-Quan; WO2015/131100; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 618-91-7, A common heterocyclic compound, 618-91-7, name is Methyl 3-iodobenzoate, molecular formula is C8H7IO2, 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: A mixture ofmethyl 3-iodobenzoate (1 mmol), corresponding amine (3 mmol), K2CO3(4 mmol), CuI (0.2 mmol) and L-proline (0.4 mmol) in 15 mL of DMSO was heatedat 60 C for 8 h. The cooled mixture was pour into 150 ml water, and extractedwith ethyl acetate (3 × 15 mL), the organic fractions were combined, washedwith saturated brine (2 × 15 ml) prior to drying over anhydrous sodium sulfate.After filtration and concentrate using a rotary evaporator, the residue was purified by silica gel column chromatographyusing a mixture of petroleum ether/ethyl acetate (20 : 1, v/v) as eluent toafford the desired product.

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; Li, Zheng; Pan, Miaobo; Su, Xin; Dai, Yuxuan; Fu, Mian; Cai, Xingguang; Shi, Wei; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 24; 9; (2016); p. 1981 – 1987;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com