Month: February 2021

Electric Literature of 5471-81-8,Some common heterocyclic compound, 5471-81-8, name is Methyl 4-iodo-3-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.

(c) Synthesis of 3-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylthio)benzoic acid In a manner similar to Example 2(a), by the reaction of 2.4 g (11 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylthiol with 3 g (11 mmol) of methyl 3-methyl-4-iodobenzoate, 1.96 g (51%) of 3-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylthio)benzoic acid of melting point 195-6 C. was directly obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-iodo-3-methylbenzoate, its application will become more common.

Reference:
Patent; Centre International de Recherches Dermatologiques Galderma; US6162815; (2000); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 103962-05-6, These common heterocyclic compound, 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, 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.

Resin 3 (120 mg, 0.084 mmol) was swelled in DCM (2 mL) for 1 h and drained. A solution of 4-(trifluoromethoxy)iodobenzene 4 (96.8 mg, 0.336 mmol) and Et3N (150 mL, 1.10 mmol) in DMF (2.0 mL) was purged with a streamof N2 bubbles for two minutes and added to the resin. After mixing for 5 min, PdCl2(PPh3)2 (18.0 mg, 0.025 mmol) andCuI (8.0 mg, 0.042 mmol) were added and the mixture shaken for 24 h. The resin was drained, washed with DMF (3 32 mL), DCM (3 3 2 mL) and cleaved with 10percent TFA/DCM (2.0 mL) for 20 min. The solution was collected and the resinwas rinsed with additional 10percent TFA/DCM (10 mL). The cleavage fractions were combined, treated with neat TFA (3.0mL), stirred for 1 h at rt and concentrated by rotary evaporation to give a crude brown residue. Purification by RP-HPLC(C18 column, CH3CN gradient 5-55percent, 0.1percent TFA, UV analysis 300 nm, 28 min) and lyophilization of the collected fractionsafforded 9.0 mg (25percent yield) of (1S)-N-(2-amino-1-hydroxycarbamoyl-ethyl)-4-(4-trifluoromethoxy-phenylethynyl)-benzamideas a white solid. LRMS (ES+) m/z 408.0 (C19H16F3N3O4 + H requires 408.11); RP-HPLC (300 nm, 28 min run)18.0 min.

The synthetic route of 103962-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Washington; Novartis Vaccines and Diagnostics, Inc.; Andersen, Niels H.; Bowman, Jason; Erwin, Alice; Harwood, Eric; Kline, Toni; Mdluli, Khisimuzi; Ng, Simon; Pfister, Keith B.; Shawar, Ribhi; Wagman, Allan; Yabannavar, Asha; EP2295402; (2015); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 1022128-96-6, name is 2-Bromo-6-iodobenzoic 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 1022128-96-6, COA of Formula: C7H4BrIO2

9.1 (7.32 g, 22 mmol) was dissolved in 40 mL of tetrahydrofuran, 4 mL of thionyl chloride and a catalytic amount of N,N-dimethylformamide After reacting for 3 hours, the reaction solution was spun off, and the residue was added with 40 mL of tetrahydrofuran, and ammonia was added dropwise with stirring in an ice bath. 33 mL of water was allowed to stand at room temperature for 3 hours. Extract with ethyl acetate and wash with saturated sodium bicarbonate. The organic layer is dry and concentrated. With a small amount of dichloromethane and purified by recrystallization from n-hexane to give a large number of white solid 9.2 6.09g, the yield was 85%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-6-iodobenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; East China University of Science and Technology; Wang Wei; Chen Xiaobei; Shen Zuyuan; Qian Pengfei; Geng Huihui; (24 pag.)CN109942505; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 620621-48-9, These common heterocyclic compound, 620621-48-9, name is Methyl 2-chloro-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.

Intermediate 2: Methyl 2-chloro-5-pyridin-2-ylbenzoate; A suspension of methyl 2-chloro-5-iodobenzoate (8.0 g, 27 mmol), 2- pyridineboronic acid N-phenyldiethanolamine ester (14.5 g, 54 mmol), palladium acetate (0.30 g, 1.35 mmol), potassium carbonate (7.46 g, 54.0 mmol), triphenylphosphine (1.42 g, 5.4 mmol) and copper iodide (2.06 g, 10.8 mmol) in THF (100 mL) was heated at 65 0C overnight under nitrogen. The reaction mixture was cooled, filtered through CeliteR and concentrated in vacuo, then the residue was suspended in DCM (250 mL) and filtered through Celite. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel eluting with EtOAc/isohexane (0 – 50%) to give the title compound as a solid (3.0 g, 49%):^ NMR 53.90 (3H, s), 7.39 – 7.43 (IH, m), 7.69 (IH, d), 7.89 – 7.95 (IH, m), 8.05 (IH, d), 8.24 – 8.28 (IH, m), 8.54 (IH, d), 8.68 – 8.70 (IH, m);MS 248.

The synthetic route of 620621-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; AstraZeneca UK Limited; WO2009/47558; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

148870-57-9, name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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: 148870-57-9

Based on EP 0 534 859 [0053] A solution of the (d) camphorsulphonate salt obtained in Example 4 in ethyl acetate is brought to basic pH using sodium hydroxide and then the organic phase is separated off, washed, dried over Na2SO4 and evaporated. [0054] A mixture composed of 5.6 g of potassium carbonate, 2.2 g of the above amine in 100 mL of acetone and 4 g of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is then refluxed for 18 hours. [0055] The solvent is evaporated off in vacuo, and the residue is taken up in ethyl acetate and then extracted with 3N hydrochloric acid. [0056] The aqueous phase separated off is brought to basic pH using sodium hydroxide and is then extracted with ethyl acetate. After washing until neutral and drying over MgSO4, evaporation in vacuo is carried out to obtain 4.5 g of an oil which is purified on a silica column using a mixture of dichloromethane/methanol (90/10) as eluant. [0057] Yield=64%

The synthetic route of 148870-57-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LES LABORATOIRES SERVIER; CARRANZA, Maria Del Pilar; GARCIA ARANDA, Maria Isabel; GONZALEZ, Jose Lorenzo; SANCHEZ, Frederic; US2014/163220; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 13194-67-7, These common heterocyclic compound, 13194-67-7, name is 4-Fluoro-2-iodo-1-methylbenzene, 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.

N-Bromosuccinimide (NBS, 3.77 g, 21.2 mmol) and benzoyl peroxide (77 mg,0.32 mmol) were added to a solution of 4-fluoro-2-iodo-1-methylbenzene 10d (5 g, 21.2 mmol) inCCl4 (55 mL). The mixture was heated to reflux for 60 hours then cooled to room temperature. The mixture was concentrated under reduced pressure. Purification over silica eluting with pentane provided the title compound as a white solid (3.67 g, 52% yield). 1H NMR (400MHz, CDCl3):d 7.57 (dd, 1H), 7.45 (dd, 1H), 7.06 (m, 1H), 4.58 (s,2H); Also a known commercially available compound.

Statistics shows that 4-Fluoro-2-iodo-1-methylbenzene is playing an increasingly important role. we look forward to future research findings about 13194-67-7.

Reference:
Article; Roberts, Lee R.; Corbett, Matthew S.; Fussell, Steven J.; Hitzel, Laure; Jessiman, Alan S.; Mason, Helen J.; Osborne, Rachel; Ralph, Michael J.; Stennett, Adam S.D.; Wheeler, Simon; Storer, R. Ian; Tetrahedron Letters; vol. 56; 47; (2015); p. 6546 – 6550;,
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 31599-61-8 as follows. COA of Formula: C8H9I

General procedure: In the flame-dried Schlenk flask (50 mL), equipped with magnetic stirrer and inert gas inlet secondary phosphine oxide 18 (0.546 g, 0.003 mol) was dissolved in toluene (5 mL). Then, aryl iodide (3,4-dimethyliodobenzene (0.696 g, 0.426 mL, 0.003 mol) or 4-iodotoluene (0.655 g, 0.003 mol)) was added, followed by CuI (0.057 g, 0.300 mmol), alpha-phenylethylamine (0.073 g, 0.077 mL, 0.600 mmol) and K2CO3 (0.829 g, 0.006 mmol). The mixture was heated at reflux for 24 h, then cooled to room temperature. Saturated NH4Cl solution (15 mL) was then added and the mixture was extracted with CHCl3 (3¡Á40 mL). The organic phase was dried over MgSO4 and evaporated and the residue was purified by flash chromatography using CHCl3:MeOH 50:1 as eluent yielding 15b (0.808 g, 94%) as white solid or 15e (0.727 g, 89%) as pale yellow solid.

According to the analysis of related databases, 31599-61-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Stankevi?, Marek; Pisklak, Jolanta; W?odarczyk, Katarzyna; Tetrahedron; vol. 72; 6; (2016); p. 810 – 824;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

202982-67-0, name is 4-Chloro-3-fluoroiodobenzene, 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. Computed Properties of C6H3ClFI

To a solution of 1-chloro-2-fluoro-4-iodobenzene (5.72 g, 22.67 mmol) in 1, 4-dioxane (150 mL) was added 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (6.00 g, 22.67 mmol), Pd (dppf) Cl2 (2.47 g, 3.38 mmol) and Cs2CO3 (11.00 g, 33.83mmol) and the mixture was heated at 80 for overnight. Then evaporated the solvent under reduced pressure and the residue was purified by column chromatography (PE: EA = 20: 1) to give product as a clear oil (4.06 g in 67% yield). 1H NMR (DMSO-d6) deltaH 7.51 (t, J= 8.0 Hz, 1H), 7.46 (m, 1H), 7.28 (m, 1H), 7.12-7.20 (m, 1H), 3.91 (s, 4H), 2.51-2.56 (m, 2H), 2.34-2.40 (m, 2H), and 1.80 (t, J = 6.8 Hz, 2H).

The synthetic route of 202982-67-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHANG, Guoliang; ZHOU, Changyou; (353 pag.)WO2018/54365; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 51560-21-5,Some common heterocyclic compound, 51560-21-5, name is 1,4-Diiodo-2,5-dimethoxybenzene, molecular formula is C8H8I2O2, 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: according to the Mizoroki-Heck reaction (Scheme 1). First; by thecoupling between 4-substituted styrenes and dibromo or diiodobenzenes(Method A, Scheme 1), and second; the reaction between4-substituted bromo or iodobenzenes with 1,4-divinylbenzene(Method B, Scheme 1).The general procedure is as follows: 2.05 equivalents of thecorresponding styrene and 1 equivalent of 1,4-dibromo or 1,4-diiodobenzene (Method A, to OPVs 1a-d and 2a-f) or 2.05 equivalentsof the appropriate aryl halide and 1 equivalent of 1,4-divinylbenzene (Method B, to OPVs 1e-h), were placed in a 10 mLheadspace crimp vial equipped with a magnetic stir bar. Then, forboth methods, it was added 0.01 equivalents (1 mol%) of Pd(dba)2,0.1 equivalents (10 mol%) of P(OPh)3 and 5 equivalents of TEA. Thevial was sealed with a PTFE/silicone septum with aluminum capand purged-saturated with N2, then 2 mL of solvent was injected(dry DMF for OPVs-series 1 and 1,4-dioxane for OPVs-series 2,Scheme 1) and the system was purged once again with N2. Thereaction mixture was vigorously stirred at 110 C during 48 h forOPVs-series 1 and 24 h for OPVs-series 2. After finished, highlyfluorescent solid products were obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Diiodo-2,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Estrada, Sandra E.; Ochoa-Puentes, Cristian; Sierra, Cesar A.; Journal of Molecular Structure; vol. 1133; (2017); p. 448 – 457;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 77317-55-6,Some common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, molecular formula is C8H8INO2, 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 2: Synthesis of methyl 5-iodo-2-(nitro amino) benzoatewherein X is I and R is Me. One hundred g of methyl 2-amino-5-iodobenzoate was dissolved in 1000 ml of acetic acid. Then 100 ml of fuming nitric acid was added to the reaction solution at 150C slowly so that the internal temperature did not exceed 2O0C. The reaction solution was stirred for 30 minutes. Afterwards, 110 ml of acetic anhydride was added to the reaction solution at 2O0C or less, followed by stirring for 1 hour. Then the reaction solution was poured into 2 L of ice water, stirred for 30 minutes, and filtered to obtain 104 g (yield: 90%) of the compound of interest which is in a yellowish solid: 1H NMR (300 MHz, DMSO), delta 8.19 (d, IH, J=2Lambda Hz), 8.07 (dd, IH ,J=8.7, 2.1 Hz), 7.21 (d, IH, J=8.7 Hz), 3.80 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-5-iodobenzoate, its application will become more common.

Reference:
Patent; PHARMACOSTECH CO., LTD.; KIM, Jae Won; CHA, Young Gwan; RYU, Hyung Chul; KIM, Sun Joo; KIM, Sang Hyun; JEON, Tae Hong; WO2010/67912; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com