Category: 77317-55-6

77317-55-6, A common compound: 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Preparation 49 Methyl 5-Iodo-2-((methylsulfonyl)amino)benzoate [BW.2] To a solution of 5-iodoanthranilic acid methyl ester (1.00 g) and triethylamine (1.01 mL) in CH2Cl2 (25 mL) is added methanesulfonyl chloride (0.59 mL) at 0 C. The ice bath is removed and after 3 h at room temperature the solution is poured into water (20 mL) and extracted with CH2Cl2 (2*20 mL). The organic layers are combined, dried over MgSO4 and the solvent removed in vacuo. The resulting residue is dissolved in CH3OH (20 mL) and sodium methoxide (20 mL) is added. After 45 min, the solvent is removed in vacuo. The residue is diluted with Et2O (20 mL) and washed with water (20 mL). The organic layer is separated, dried over MgSO4, filtered, and concentrated in vacuo. The crude black liquid is purified by silica gel column chromatography (4/1, hexanes/EtOAc) to afford 0.58g (46%) of the title compound as a brown solid. Physical characteristics: m.p. 119-120 C.; 1H NMR (300 MHz, CDCl3) delta 10.41, 8.36, 7.82, 7.52, 3.94, 3.06; IR (diffuse reflectance) 1700, 1682, 1483, 1385, 1335, 1328, 1307, 1249, 1213, 1159, 1147, 1093, 1086, 978, 971 cm-1; MS (FAB) m/z 356 (MH+); HRMS (FAB) m/z 355.9447 (C9H10INO4S+H). Anal. Found: C, 30.49; H, 2.88; N, 3.96.

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 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bundy, Gordon L.; Ciske, Fred L.; Genin, Michael J.; Heasley, Steven E.; Larsen, Scott D.; Lee, Byung Hyun; May, Paul D.; Palmer, John R.; Schnute, Mark E.; Vaillancourt, Valerie A.; Thorarensen, Atli; Wolf, Allison J.; Wicnienski, Nancy Anne; Wilhite, David; US2002/25960; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, 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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, A new synthetic method of this compound is introduced below.

2-Amino-5-iodo-benzoic acid methyl ester (14.00 g) was dissolved in dry THF (50 mL) and 1 M diisobutylaluminium hydride in THF (165 mL) was added dropwise to this solution at -300C. The solution was then stirred at -15C for 1 h. To this mixture MeOH (50 mL) was added portionwise, maintaining the temperature of the solution below -5C. The resulting mixture was then left at -15C for 18 h. The formed solid was filtered off and washed with MeOH. The organic phase was dried and the solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 1-5% methanol in dichloromethane) to give the title compound (9.70 g); ESMS m/z 249.9 [M+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; GLAXO GROUP LIMITED; GLAXOSMITHKLINE ISTRAZIVACKI CENTAR ZAGREB D.O.O.; WO2007/54296; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, The chemical industry reduces the impact on the environment during synthesis 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, I believe this compound will play a more active role in future production and life.

5-Iodoanthranilic acid methyl ester (1 g, 3.61 mmol) and formamide (2 ml) were used as a reactant and solvent, then the reaction was carried out in a microwave reactor for 1 hour at 200 C in a microwave reactor vial. After the completion of the reaction, the resulting solid compound was washed with water and then the water was removed from the oven at 100 C for about 1 hour to obtain Compound 1 (784 mg, 2.88 mmol, 80%).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-5-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chung Ang University industry Academic Cooperation Foundation; Min, Kyung-Hoon; Lee, Seul; (24 pag.)KR2017/15848; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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: CuCl (1.50 mg, 0.0150 mmol), DPEPhos (8.10 mg, 0.0150 mmol) and KOt-Bu (1.70 mg,0.0150 mmol) were added to a 8 mL vial charged with a magnetic bar. The vial was sealedwith a cap (phenolic open top cap with gray PTFE/silicone) and purged by N2 gas for 5 min.Toluene (0.8 mL) and methyl 2-aminobenzoate (1a) (46.6 L, 0.360 mmol) were added to themixture, which was allowed for 10 min. And then a solution of phenyl vinyl sulfone (2) (50.5mg, 0.300 mmol) in toluene (0.7 mL) was added to the reaction solution. After stirring atroom temperature for 5 h, THF (5 mL) was added and the reaction was allowed to cool to 0C (ice bath). After addition of KOt-Bu (101 mg, 0.900 mmol), the resulting solution wasallowed to stir for further 1 h at 0 C. After that time, the reaction was quenched with asaturated aqueous solution of NH4Cl (1 mL) and NaHCO3 (2 mL) and washed with EtOAc (7x 3 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated invacuo. The crude product was purified by silica gel column chromatography (CH2Cl2/EtOAc,8:1) to afford the desired product 4a (76.8 mg, 0.267 mmol, 89% yield) as a yellow solid.

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 77317-55-6.

Reference:
Article; Kang, Seongil; Yoon, Hongju; Lee, Yunmi; Chemistry Letters; vol. 45; 12; (2016); p. 1356 – 1358;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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.

Under N2, a suspension of methyl 2-amino-5-iodobenzoate (4) (2.77 g, 10 mmol), Pd(PPh3)4 (1.159 mg, 1 mmol), CuI (381 mg, 2 mmol), Et3N (4.2 mL, 30 mmol) and propargyl alcohol (1.75 ml, 30 mmol) in DMF (20 mL) was stirred at rt for 15 h. TLC analysis (petrol ether: ethyl acetate 1:1) indicated the fully consumption of starting material. The reaction was quenched with 200 ml sat. NaCl solution. Ethyl acetate: petrol ether 1:1 (200 ml) was added to the mixture and the aqueous layer was extracted with ethyl acetate:petrol ether 1:1 three times. After drying the combined organics over MgSO4, the solution was concentrated and purified by silica gel chromatography (petrol ether:ethyl acetate 80:20 to ethyl acetate), giving Compound 5 as a yellow oil (1.88 g, 92%). 1H NMR (CDCl3) delta 3.78 (s, 3H), 4.25 (s, 2H, CCH?2), 7.27-7.36 (m, 2H, arom.H), 7.58-7.65 (m, 1H, arom.H).

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 77317-55-6.

Reference:
Patent; Illumina, Inc.; Illumina Cambridge Limited; Wu, Xiaolin; Smith, Randall; Shieh, Peyton; Beierle, John M.; George, Wayne N.; Lawrence, Elliot John; Mao, Jie; Liu, Xiaohai; (62 pag.)US2019/352327; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, A common compound: 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a stirred solution of methyl 6-iodoanthranilate (53) (4.46 g, 16.1 mmol) in ethyl orthoformate (8.92 mL, 53.5 mmol) was added 2,2-dimethyl-1,3-dioxane-4,6-dione (1.16 g, 8.05 mmol). The mixture was stirred at 80 C for 45 min. After cooling to room temperature, the yellow precipitate was filtered and washed with ethanol (2 x 10 mL) to give methyl 2-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-ylidenemethyl)amino]-5-iodobenzoate (54) (3.31 g, 7.68 mmol) as a yellow solid. Yield 95%; mp 206-208 C; IR (KBr) nu 1198, 1227, 1251, 1284, 1429, 1585, 1607, 1685, 3100-3250 cm-1; 1HNMR (200 MHz, CDCl3) delta 1.07 (s, 6H, (CH3)2C), 3.98 (s, 3H, CH3O), 7.23 (d, 1H, J = 8.8 Hz), 7.86 (dd, 1H, J = 2.0, 8.8 Hz, H-3), 8.38 (d, 1H, J = 2.0 Hz, H-4), 8.65 (d, 1H, J = 14.0 Hz, C=CH-NH), 13.1 (d, 1H, J = 14.0 Hz, NH); 13C NMR (50 MHz, CDCl3) delta 27.2 ((CH3)2C), 53.2 (CH3O), 88.5 (C-5), 89.9 (C=CH-NH), 105.1 ((CH3)2C), 117.6 (C-3), 119.7 (C-1), 139.5 (C-2), 140.8 (C-6), 143.2 (C-4), 150.4 (C=CH-NH) 163.6 (CO), 164.0 (CO), 165.3 (CO); ESI-MS m/z 373.89 [M-CH3O-CO + H]+.

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 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Billaud, Emilie M.F.; Maisonial-Besset, Aurelie; Rbah-Vidal, Latifa; Vidal, Aurelien; Besse, Sophie; Bequignat, Jean-Baptiste; Decombat, Caroline; Degoul, Francoise; Audin, Laurent; Deloye, Jean-Bernard; Dolle, Frederic; Kuhnast, Bertrand; Madelmont, Jean-Claude; Tarrit, Sebastien; Galmier, Marie-Josephe; Borel, Michele; Auzeloux, Philippe; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 818 – 838;,
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 77317-55-6 as follows. 77317-55-6

Examples 13 to 21:; The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the type of the anthranilic acid derivative was changed. The results are shown in Table 4.

According to the analysis of related databases, 77317-55-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; EP1997812; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, Adding a certain compound to certain chemical reactions, such as: 77317-55-6, name is Methyl 2-amino-5-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 77317-55-6.

To methyl 2-amino-5-iodobenzoate (i-a) (15 g, 54 mmol) was added 200 mL of CH2Cl2, followed by DIEA (9.4 mL, 54 mmol) and a catalytic amount of DMAP. Ethyl 4-chloro-4-oxobutanoate (Rc = Rd = H) (8.5 mL, 60 mmol) was added, and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was then poured into 250 mL H2O, and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford ii-a (22 g, 99%) as a pale yellow solid: MS m/z = 406 (M+H).

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 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/41773; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, 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. 77317-55-6 name is Methyl 2-amino-5-iodobenzoate, 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.

General procedure: A mixture of substituted iodobenzene (2 mmol), (5-formylfuran-2-yl)boronic acid (420 mg, 3mmol, 1.5 equiv), Pd(Ph3P)2Cl2 (0.1 mmol, 0.05 equiv, 70 mg) and potassium carbonate (6 mmol,3 equiv, 828 mg) in dioxone/H2O (6 mL/2 mL) was stirred at 100 C under argon atmosphereuntil the starting material was consumed (typically 20 h). The reaction mixture was then diluted with 25 mL of saturated brine. The mixture was then extracted with EtOAc (25 mL ¡Á 2), and the organic layers were combined, dried over Na2SO4. The concentrated crude product was purifie dby column chromatography to afford c2a-e. The second step is the same as procedure A.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-5-iodobenzoate, and friends who are interested can also refer to it.

Reference:
Article; Liang, Dongdong; Robinson, Elizabeth; Hom, Kellie; Yu, Wenbo; Nguyen, Nam; Li, Yue; Zong, Qianshou; Wilks, Angela; Xue, Fengtian; Bioorganic and Medicinal Chemistry Letters; vol. 28; 6; (2018); p. 1024 – 1029;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The chemical industry reduces the impact on the environment during synthesis 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, I believe this compound will play a more active role in future production and life. 77317-55-6

Example 23 This example describes the synthesis of 2-iodo-9-trifluoromethyl-7,12-dihydro-indolo[3,2-d][1]benzazepin-6(5H)-one. A solution of methyl succinyl chloride (3011 mg, 20 mmol) in toluene (10 mL) was added dropwise by means of a dropping funnel to a mixture of 2-amino-5-iodobenzoic acid methyl ester (4156 mg, 15 mmol), pyridine (1.7 mL), and toluene (10 mL) with stirring and cooling. The resulting suspension was refluxed for 3 hours. After cooling to room temperature, water (15 mL) was added. The organic layer was separated and washed successively with 10% hydrochloric acid (5 mL) and 5% aqueous sodium carbonate solution (5 mL). Subsequently, the organic layer was dried over sodium sulfate and evaporated. The residue was crystallized from ethanol to yield 72% colorless crystals of precursor 5-iodo-2-[(4-methoxy-1,4-dioxobutyl)amino]-benzoic acid methyl ester, mp. 133 C.; ir (KBr): 3250 (NH), 1730/1720/1680 (C=O); 1H-nmr (DMSO-d6, 400 MHz): delta (ppm)=2.59-2.69 (m, AA’BB’, 4H, CH2-CH2), 3.60 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 7.91 (dd, 1H, 8.7/2.0 Hz), 7.99 (d, 1H, 8.7 Hz), 8.14 (d, 1H, 2.0 Hz), 10.53 (s, 1H, NH); 13C-nmr (DMSO-d6, 100.6 MHz): delta (ppm)=28.3, 31.4, 51.3, 52.5, 86.3, 120.1, 123.2, 138.3, 138.8, 141.9, 166.1, 170.1, 172.5; C13HI4INO5 (391.17); Calcd. C 39.9, H 3.6, N 3.6,1 32.4; Found C 39.9, H 3.7, N 3.6,1 32.4.

The chemical industry reduces the impact on the environment during synthesis 77317-55-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zaharevitz, Daniel W.; Gussio, Rick P.; Jalluri, Ravi K.; Sausville, Edward A.; Kunick, Conrad; Meijer, Laurent; US2002/42412; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com