Month: May 2021

Reference of 773855-64-4, 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. 773855-64-4 name is 1-Fluoro-4-iodo-2-methoxybenzene, 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.

Dissolve l-fluoro-4-iodo-2-methoxybenzene, (prepared as described in PREPARATION 47), (1. 0 g, 4. 0 mmol) in triethylamine (15 mL, 108 mmol) and add 3- ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (500 mg, 3. 8 mmol) followed by bis (triphenylphosphine) palladium (II) dichloride (100 mg, 0. 14 mmol) and copper (I) iodide (60 mg, 0. 32 mmol). Stir for 18 h at room temperature, concentrate and purify by silica gel chromatography, eluting with 3 : 1 hexanes : ethyl acetate. Further purify on silica gel, eluting with 9 : 1 dichloromethane : ethyl acetate, to give the title compound as a white solid (650 mg, 65%). 1HNMR (300 MHz, CDC13) 6 3. 88 (s, 3H), 3. 92 (s, 3H), 6. 98-7. 15 (m, 3H), 7. 29-7. 31 (m, 1H), 8. 27 (d, J = 2. 8 Hz, 1H), 8. 37 (d, J = 1. 5 Hz, 1H) ; MS (APCI) : m/z= 258 [M+H] +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Fluoro-4-iodo-2-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

264927-52-8, name is 2-Chloro-4-fluoro-5-iodobenzoic 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. HPLC of Formula: C7H3ClFIO2

To a stirred solution of compound 3 (2.200 g, 7.33 mmol) in anhydrous DMF (20 mL) was added K2CO3 (0.846 g, 8.06 mmol) and isopropyl iodide (1.870 g, 10.99 mmol) in sequence at room temperature. The resulting mixture was stirred at the same temperature for 6 h and saturated NH4Cl(aq) (10 mL) was added to quench the reaction. The aqueous layer was separated and extracted with EtOAc (20*3 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to give the crude residue, which was purified by flash chromatography on silica gel with EtOAc/n-hexane (1:19) to afford compound 5 (2.407 g, 96% yield) as white solid. Mp 43-44 C; IR (neat): 1732, 1714, 1585, 1558, 1463, 1371, 1284, 1271, 1255 cm-1; 1H NMR (500 MHz, CDCl3): delta=8.23 (d, J=6.5 Hz, 1H), 7.19 (dd, J=7.5, 1.0 Hz, 1H), 5.28 (septet, J=6.0 Hz, 1H), 1.41 (d, J=6.0 Hz, 6H); 13C NMR (125 MHz, CDCl3): delta=163.1, 163.0 (d, J=252.5 Hz), 141.9 (d, J=2.5 Hz), 135.5 (d, J=10.0 Hz), 128.4 (d, J=3.7 Hz), 118.4 (d, J=26.2 Hz), 78.6 (d, J=26.2 Hz), 69.9, 21.8 (2*CH3); 19F NMR (470 MHz, CDCl3): delta=-89.5; HRMS (EI) m/z [M]+ calcd for C10H9ClFIO2: 341.9320; found: 341.9321.

The synthetic route of 264927-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hsieh, Min-Tsang; Lin, Hui-Chang; Kuo, Sheng-Chu; Tetrahedron; vol. 72; 39; (2016); p. 5880 – 5885;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 136618-42-3, A common heterocyclic compound, 136618-42-3, name is Benzyl 4-iodobenzoate, molecular formula is C14H11IO2, 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 8: Phenvlmethvl 4-(4-amino-6-methvl-1H-indazol-1-vl)benzoate; 6-Methyl-1 W-indazol-4-amine (5.48g, 37.3mmol), copper (I) iodide (71 mg, 0.37mmol), trans-1 ,2-cyclohexanediamine (420mg, 0.37mmol) and tripotassium phosphate (16.6g, 78.3mmol) were added to a solution of phenylmethyl 4-iodobenzoate (12.61g, 37.3mmol) in 1 ,4-dioxane (2OmL). More 1 ,4-dioxane (3OmL) was added and the mixture heated under reflux for 3 hours 15 min and then allowed to gradually cool to room temperature and partitioned between water and ethyl acetate. The aqueous phase was extracted once more with ethyl acetate and the combined organic extracts were washed with brine and dried and evaporated to give a brown solid (13.58g). This crude product was combined with material (0.66g) from a similar reaction and purified by column chromatography on silica gel (Merck 7734, 50OmL) eluting initially with 10% and finally with 20% ethyl acetate in dichloromethane. Evaporation of product containing fractions gave a brown-yellow solid (5.12g) which was dissolved in ethyl acetate (4OmL) at 60 and warm cyclohexane (7OmL) was added. The mixture was then cooled in ice and the precipitate was collected by filtration, washed with cyclohexane:ethyl acetate (4:1 , 4OmL) and dried to give the title compound as a beige solid (4.29g). LCMS (System A): tRET = 3.77 min; MNH4+ = 358

The synthetic route of 136618-42-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/50243; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 42048-11-3, name is 2-Chloro-6-iodotoluene, 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. Safety of 2-Chloro-6-iodotoluene

Under a protective atmosphere of inert gas, Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, were added to a 4.0 mL reaction flask equipped with a magnetic stir bar. 10 mol%), 2-methyl-1-chloro-3-iodobenzene (0.2 mmol, 1.0 equiv.), ethylene oxide (0.6 mmol, 3.0 equiv.) and dry N-methylpyrrolidone(1.0 mL). The reaction flask was capped and stirred at room temperature for about 5 minutes, after which the mixture was heated to 80 C and stirred for 24 hours.After the reaction vessel was cooled to room temperature, it was quenched with water (10 mL), extracted with methyl tert-butyl ether (3×10 mL), dried over Na2SO4Filter and concentrate under vacuum. Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 20:1 (v/v) to afford 7-methyl-6-Chloro-2,3-dihydrobenzofuran 22 mg (yellow oily liquid, yield 64%).

The synthetic route of 2-Chloro-6-iodotoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 1309788-50-8, name is 3-Iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole, 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 1309788-50-8, SDS of cas: 1309788-50-8

To a solution of 3-iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole (41 g, 147 mmol), triethylamine (22 ml, 155 mmol) and 4-dimethylaminopyridine (824 mg, 7 mmol) in tetrahydrofuran (163 ml) was added dropwise a solution of di-tert-butyl dicarbonate (34 g, 155 mmol) in tetrahydrofuran (41 ml) at room temperature over 40 min, and the mixture was stirred for 30 min. Then, the reaction mixture was is concentrated under reduced pressure. The residue was slurry-washed in hexane (130 ml) at 60 C. and ice-cooled. The crystals were collected by filtration, washed with hexane, and dried under reduced pressure to give the title compound (53 g, yield 95%).1H-NMR (400 MHz, DMSO-d6) delta: 0.95 (s, 6H), 1.46 (t, 2H, J=6.38 Hz), 1.56 (s, 9H), 2.23 (t, 2H, J=6.26 Hz), 2.63 (s, 2H).

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, 3-Iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JAPAN TOBACCO INC.; US2011/306599; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 1309788-50-8, name is 3-Iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole, 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. name: 3-Iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole

Step 4: iert-Butyl 3-iodo-6,6-dimethyl-4,5,6,7-tetrahydro-lH-indazole-l-carboxylate: To a stirred solution of step 3 intermediate (3.9 g, 14.124 mmol) in dry tetrahydrofuran (20 ml), triethylamine (2.08 ml, 14.83 mmol), 4-dimethylaminopyridine (68 mg, 0.565 mmol) were added followed by addition of di-tert-butyl bicarbonate (3.23 g, 14.83 mmol) at room temperature and reaction mixture was stirred for 1 h at same temperature. The solvent was evaporated under reduced pressure and product was purified by column chromatography to yield 5.24 g of product as a pale yellow solid. 1H NMR (300 MHz, CDC13): delta 1.00 (s, 6H), 1.50 (t, / = 6.6 Hz, 2H), 1.59-1.69 (m, 9H), 2.31 (t, / = 6.3 Hz, 2H), 2.67 (s, 2H).

The synthetic route of 3-Iodo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; KUMAR, Sukeerthi; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; WO2014/41518; (2014); 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. 14192-12-2, name is 2,5-Diiodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,5-Diiodobenzoic acid

To an oven-dried seal tube, was added 2,5-diiodobenzoic acid 6b (74.8 mg, 0.2 mmol), CuI (3.8 mg, 0.02 mmol) and K2CO3 (55.2 mg, 0.4 mmol). The reaction tube was evacuated and backfilled with argon. 2-Propanol (1.0 mL), ethylene glycol (22.3 muL) and thiol 5 (30 muL, 0.22 mmol) were added by syringes at room temperature. The tube was heated to 80 oC and stirred for 68 h. The reaction mixture was then allowed to reach room temperature. The reaction mixture was then filtered and concentrated in vacuo. The crude product was purified using CombiFlash automated chromatography system (methanol / methylene chloride, 0% to 10%) to afford the desired product 7b as white 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 14192-12-2.

Reference:
Article; Zheng, Pinguan; Lieberman, Brian P.; Ploessl, Karl; Lemoine, Laetitia; Miller, Sara; Kung, Hank F.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 869 – 872;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 930599-57-8,Some common heterocyclic compound, 930599-57-8, name is 4-Iodo-2-methyl-1-(trifluoromethyl)benzene, molecular formula is C8H6F3I, 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 intermediate 164d (3.5 g, 12.24 mmol, 1.00 equiv) in CC14 (40 mL) at 60 C was added benzoyl peroxide (1.7 g, 7.02 mmol, 0.57 equiv) followed by the batch-wise addition of NBS (2.37 g, 13.32 mmol, 1.09 equiv) and the reaction stirred at reflux overnight. The solids were filtered out and the filtrate concentrated to afford 1.6 g (36%) of intermediate 164e as a red oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-2-methyl-1-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; ARDELYX, INC.; LEWIS, Jason, G.; REICH, Nicholas; CHEN, Tao; JACOBS, Jeffrey W.; CHARMOT, Dominique; NAVRE, Marc; FINN, Patricia; CARRERAS, Christopher; SPENCER, Andrew; WO2013/96771; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 7212-28-4, name is 2-Iodo-N-phenylacetamide, 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. COA of Formula: C8H8INO

General procedure: 0.4 g (1.61 mmol) of 10, 1.93 mmol of 3a-j and 0.55 g (4.01 mmol) of K2CO3 were combined and refluxed in 20 ml acetone for 2 h. Then the solvent was reduced under reduced pressure. The crude product was washed with water, filtered and dried, followed by recrystallization from petroleum ether and ethyl acetate.

The synthetic route of 2-Iodo-N-phenylacetamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Wukun; Hua, Jie; Zhou, Jinpei; Zhang, Huibin; Zhu, Haiyang; Cheng, Yanhua; Gust, Ronald; Bioorganic and Medicinal Chemistry Letters; vol. 22; 15; (2012); p. 5008 – 5012;,
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. 3824-21-3, name is 2-Fluoro-4-iodo-1-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H6FIO

2-Fluoro-4-iodo-1-methoxybenzene a16 (0.0252 g, 0.10 mmol), acridine photosensitizer (A) (0.0029 g, 0.005 mmol) and L-valine were added sequentially under argon atmosphere. Ethyl b1 (0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated for 48 hours under a 6W blue light at room temperature.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluting solvent: (V) petroleum ether / (V) ethyl acetate = 30/1.Yellow liquid (33) (0.0100 g, 87%) was obtained.

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 3824-21-3.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (27 pag.)CN110294685; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com