Category: 71759-89-2

Reference of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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 4-iodo-1H-imidazole (2.05 g, CAS: 7 1759-89-2) and trityl chloride (4.4 g, CAS: 76-83-5) in DMF (35 mL) was added triethylamine (3.04 mL, CAS: 121-44-8) at 0 C. The reaction mixture was slowly warmed to rt and was stuffed for 48 hours. The reaction mixturewas then poured into H20 (150 mL). The solid was filtered, washed with H20 (60 mL) and dried under reduced pressure. The resulting crude material was purified by flash chromatography using silica gel (EtOAc) to give the title compound as a white solid (4.3 g, 93%). Rf= 0.50 (10% EtOAc/hexane).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; LUEBBERS, Thomas; MARTIN, Rainer E.; MATTEI, Patrizio; NEIDHART, Werner; RICHTER, Hans; RUDOLPH, Markus; PINARD, Emmanuel; (450 pag.)WO2017/37146; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

4-lodo-1tf-imidazole (2.8g, 14.6mmol) and trityl chloride (5.Og, 20.5mmol) were dissolved in lambda/,lambda/-dimethylacetamide (45mL). The solution was cooled to 0″C and triethylamine (4mL, 29.2mmol) added slowly. The reaction mixture was slowly warmed to room temperature. After 48 hours the solution was poured to water(15OmL). The solid was filtered, washed with water, hexane and dried to give a white solid (5.7g) with a yield of 90%. The product was pure enough for the next step reaction without further purification.

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; S BIO PTE LTD; WO2009/93981; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 71759-89-2,Some common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

Step 1. 4-Iodo-l-methyl-lH-imidazole and 5-iodo-l-methyl-lH-imidazole (1205) [00394] Under an atmosphere of nitrogen at 0 C, a solution of 4-iodo-lH-imidazole (5.82 g, 30.00 mmol) in THF (50 mL) was treated with portionwise addition of sodium hydride (60% dispersion in mineral oil, 1.44 g, 36.00 mmol). After stirring for 30 min at 0 C, iodomethane was added (2.8 mL, 45.00 mmol) and the mixture was stirred for 1 h at 0 C. The reaction mixture was poured into water (100 mL) and was extracted with EtOAc (2 x 100 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 6.24 g (90%) of a -3 : 1 mixture of 4-iodo-l-methyl-lH-imidazole and 5- iodo-1 -methyl- lH-imidazole as a light yellow solid. MS (ESI) m/z 209 [M+H]+. Step 2. terf-Butyl 4-(l-methyl-lH-imidazol-4-yl)-3,6-dihydropyridine-l(2H)-carboxylate and terf-butyl 4-(l-methyl-lH-imidazol-5-yl)-3,6-dihydropyridine-l(2H)-carboxylate (1207) [00395] A -3 : 1 mixture of 4-iodo-l -methyl- lH-imidazole and 5-iodo-l-methyl-lH-imidazole (6.24 g, 30.00 mmol), fert-butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-5,6- dihydropyridine-l(2H)-carboxylate (1 1.1 g, 36.00 mmol), Pd(dppf)Cl2 CH2Cl2 (2.45 g, 3.00 mmol) and sodium carbonate (6.36 g, 60.00 mmol) in water (60 mL) and 1,4-dioxane (300 mL) was stirred under an atmosphere of nitrogen for 3 h at 80 C. After cooling to ambient temperature, the reaction mixture was poured into EtOAc (100 mL) and was washed with water (2 x 100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (eluting with a gradient of 1-5% DCM/MeOH) to afford 5 g (57%) of a -3 : 1 mixture of tert-butyl 4-(l-methyl-lH-imidazol-4-yl)- 3,6-dihydropyridine-l(2H)-carboxylate and tert-butyl 4-(l-methyl-lH-imidazol-5-yl)-3,6- dihydropyridine-l(2H)-carboxylate as a yellow oil. MS (ESI) m/z 264 [M+H]+. Step 3. tert-But l 4-(l-methyl-lH-imidazol-4-yl)piperidine-l-carboxylate and tert-butyl 4-(l- methyl-lH-imidazol-5-yl)piperidine-l-carboxylate (1209) [00396] A -3 : 1 mixture of tert-butyl 4-(l-methyl-lH-imidazol-4-yl)-3,6-dihydropyridine- l(2H)-carboxylate and tert-butyl 4-(l-methyl-lH-imidazol-5-yl)-3,6-dihydropyridine-l(2H)- carboxylate (5 g, 19.01 mmol) and palladium on carbon (10 wt. %, 5 g) in MeOH (100 mL) was evacuated and backfilled with hydrogen several times and was then charged with hydrogen. The resulting mixture was stirred for 1 h at ambient temperature before being filtered and concentrated under vacuum, resulting in 1.7 g (34%) of a -3 : 1 mixture of tert-butyl 4-(l-methyl- lH-imidazol-4-yl)piperidine-l-carboxylate and tert-butyl 4-(l-methyl-lH-imidazol-5- yl)piperidine-l-carboxylate as a yellow oil. MS (ESI) m/z 266 [M+H]+.

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; BUCKMELTER, Alexandre Joseph; IOANNIDIS, Stephanos; FOLLOWS, Bruce; GUSTAFSON, Gary; WANG, Minghua; CARAVELLA, Justin A.; WANG, Zhongguo; FRITZEN, Edward L.; LIN, Jian; (414 pag.)WO2017/87837; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 71759-89-2, name is 5-Iodo-1H-imidazole, belongs to imidazoles-derivatives 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 71759-89-2, Recommanded Product: 5-Iodo-1H-imidazole

Step 1:To a 000 mixture of 4-iodoimidazole AlOa (5.0 g, 25.8 mmol) (Synthonix) in anhydrous THF (100 mL) is added NaH (60% in oil, 1 .24 g, 30.9 mmol). The resulting mixture is stirred for 10 mm before the addition of 4-methoxybenzyl chloride (4.37 mL, 32.2 mmol) (Aldrich). This mixture is allowed to warm to RT and is stirred overnight. An aqueous solution of saturated NH4CI (50 mL) is added and this mixture is stirred for 10 mm. The mixture is extracted with EtOAc (3x) and the layers are separated. The organic layer is washed with water and brine, dried with Mg504 and concentrated to provide crude material that is purified by Combif lash (20:80 to 80:20, EtOAc/hexanes) to provide AlOb.

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, 5-Iodo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; BILODEAU, Francois; POIRIER, Maude; PARISIEN, Mathieu; KUHN, Cyrille; THIBEAULT, Carl; TRINH, Thao; WO2014/70978; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 71759-89-2, name is 5-Iodo-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 71759-89-2

EXAMPLE 47 Benzo[1,3]dioxol-5-ylmethyl-(3-[3-(4-iodo-imidazol-1-yl)-[1,2,4]thiadiazol-5-yl]-methyl-amino}-propyl)-carbamic Acid tert-butyl Ester Example 47 was prepared following the procedures described in the preparation of Example 1 using 4-iodo-1H-imidazole. [M+H]+598.90.

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; KALYPSYS, INC.; US2007/123572; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 71759-89-2 as follows. HPLC of Formula: C3H3IN2

Preparation 72 4-Iodo-1-triphenylmethyl-1H-imidazole To 4-iodo-1H-imidazole (Preparation 71, 3.0 g, 15.3 mmol) in N,N-dimethylformamide (25 ml) was added triphenylmethyl chloride (4.72 g, 16.9 mmol) and then triethylamine (2.5 ml, 18.4 mmol). After stirring at room temperature for 2.5 h, water (200 ml) was added and the reaction mixture was filtered and washed with water. The crude solid was chromatographed on silica gel eluding with hexane:ethyl acetate (5:1 and then 2:1). The material was then recrystallized from hexane and dichloromethane to give the title compound as a white solid (4.0 g, 59%). NMR (CDCl3, selected data for the free base: 6.9 (m, 1H), 7.0-7.2 (m, 6H), 7.25-7.4 (m, 10H). MS (TSP): M/Z (MH+): 436.3; C22H17129IN2+H requires 437.1.

According to the analysis of related databases, 71759-89-2, the application of this compound in the production field has become more and more popular.

Related Products of 71759-89-2, The chemical industry reduces the impact on the environment during synthesis 71759-89-2, name is 5-Iodo-1H-imidazole, I believe this compound will play a more active role in future production and life.

4-lodo-1H-imidazole (194mg, LOmmol), phenylboronic acid (158.5 mg, 1.3mmol), potassium carbonate (345mg, 2.5mmol) and Pd (PPh3)2Cl2 (42 mg, 6%) were taken up in a degassed mixture of 1 ,4-dioxane (5mL) and water (0.8mL) under an atmosphere of nitrogen. The resulting mixture was heated at 901C for 3 hours. The reaction mixture was cooled to room temperature, and taken up in ethyl acetate and water. The organic phase was separated and the aqueous layer further extracted with 3×20 ml portions of ethyl acetate. The combined ethyl acetate layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated under vacuum. The residue was purified by flash chromatography to give the product (112 mg) with a yield of 78%.

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, 5-Iodo-1H-imidazole, other downstream synthetic routes, hurry up and to see.

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 71759-89-2 as follows. Application In Synthesis of 5-Iodo-1H-imidazole

4-Iodoimidazole (0101-1) (10.0 g, 51.6 mmol, 1.0 eq.)Dissolved in 150 ml of tetrahydrofuran,Triphenylmethyl chloride (17.2 g, 61.7 mmol, 1.2 equivalents) andTriethylamine (14.5 ml, 10.4 mmol, 2.0 eq),Heat to 80C and react overnight.Cooled to room temperature, concentrated under reduced pressure, added ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Methanol and a small amount of dichloromethane were added and stirred for half an hour. The solid was collected by suction, washed twice with methanol, and vacuum dried. ,4-Iodo-1-trityl-1H-imidazole (16 g, yield: 71%) was obtained as a white solid.

According to the analysis of related databases, 71759-89-2, the application of this compound in the production field has become more and more popular.

Application of 71759-89-2, A common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, molecular formula is C3H3IN2, 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.

Step 1:To a 000 mixture of AlOa (2.0 g, 10.3 mmol) (Synthonix) in anhydrous THF (40 mL) is added NaH (60% in oil, 495 mg, 12.4 mmol). The resulting mixture is stirred for 10 mm before the addition of (3-bromo-propoxymethyl)benzene (2.3 mL, 12.9 mmol) (Chembridge-BB). The resulting mixture is allowed to warm to RT, and then is stirred overnight. An aqueous solution of saturated NH4CI (20 mL) is added, and this mixture is stirred for 10 mm. The mixture is extracted with EtOAc (3x) and the layers are separated. The organic layer is washed with water,brine, dried with MgSO4 and concentrated to provide crude material that is purified by Combif lash (20:80 to 80:20, EtOAc/hexanes) to provide A22a.

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 71759-89-2, name is 5-Iodo-1H-imidazole, 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. Computed Properties of C3H3IN2

4-iodoimidazole (5.38g, 27.72mmol) was dissolved in THF (86ml_). Trityl chloride, (8.5g, 30.49mmol) and triethylamine (7.73ml_, 55.44mmol) were added and the reaction was heated at 70 C. After 3 h, TLC showed that the reaction had gone to completion. Therefore, the reaction mixture was allowed to cool to 45 C and filtered to remove the suspended white solid. The filtrate was concentrated, redissolved in DCM (300 mL) and washed with 5 wt% aq. sodium thiosulfate solution (300 mL), which was back-extracted with DCM (150 mL). The organics were combined, dried over sodium sulfate, filtered and concentrated to yield the crude product. The white solid was taken up in EtOAc (300ml) and heated to reflux for 30 minutes. The mixture was cooled and the solid was obtained by vacuum filtration. The white solid was dried in the vacuum oven for 3 hours affording 4- iodo-1 -trityl-imidazole (6.721 g, 15.40mmol, 55.57% yield). MS Method 2: RT 2.08 min, ES+ m/z 459 [M+Na]+ H NMR (400MHz, DMSO) delta/ppm: 7.35-7.40 (m, 10H), 7.06-7.1 1 (m, 7H).

The synthetic route of 5-Iodo-1H-imidazole has been constantly updated, and we look forward to future research findings.