Tag: M.W=200-300

Application of 167479-01-8,Some common heterocyclic compound, 167479-01-8, name is tert-Butyl (3-iodopropyl)carbamate, molecular formula is C8H16INO2, 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 a nitrogen atmosphere, cesium carbonate (10.13 g, 31.07 mmol) was added to a suspension of 2-propyl[l,3]thiazolo[4,5-c]quinolin-7-ol (5.06 g, 20.7 mmol) in DMF (110 mL), and the reaction mixture was heated at 65 0C. A solution of tert-butyl 3- iodopropylcarbamate (7.08 g, 24.8 mmol) in DMF (20 mL) was added dropwise with stirring. The reaction mixture was stirred at 65 C overnight. The solvent was then removed under reduced pressure at 65 0C. The resulting solid was partitioned between dichloromethane (250 mL) and water (250 mL). The organic layer was washed EPO sequentially with saturated aqueous sodium thiosulfate (100 mL), water (100 mL), and brine (100 mL); dried over magnesium sulfate; filtered; and concentrated under reduced pressure. The resulting solid was purified by column chromatography on silica gel (eluting with 0 to 4% methanol in chloroform) to provide 5.36 g of tert-butyl 3-[(2- propyl[l,3]thiazolo[4,5-c]quinolin-7-yl)oxy]propylcarbamate as a light 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 tert-Butyl (3-iodopropyl)carbamate, its application will become more common.

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2006/86449; (2006); A2;,
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Application of 52548-63-7, A common heterocyclic compound, 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, molecular formula is C7H4FIO2, 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 B: The product of Step A (9.0 g, 34 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled in an ice bath under nitrogen. A 2.0 M solution of borane-methyl-sulfide complex (42 mL, 8.5 mmol) in tetrahydrofuran was added dropwise and the mixture was stirred for 30 minutes. The ice bath was removed and the reaction mixture was refluxed for 2 hours at 70 C. The solvent was concentrated in vacuo and the residue was dissolved in saturated ammonium chloride and extracted twice with methylene chloride. The organic extract was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the desired product (6.2 g, 73%) as an off-white solid: 1H NMR (500 MHz, CDCl3) delta 7.78-7.69 (m, 1H), 7.31-7.22 (m, 1H), 6.83-6.75 (m, 1H), 4.64 (s, 2H), 2.04 (s, 1H).

The synthetic route of 52548-63-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Molino, Bruce F.; Liu, Shuang; Guzzo, Peter R.; Beck, James P.; US2006/52378; (2006); A1;,
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Reference of 4387-36-4,Some common heterocyclic compound, 4387-36-4, name is 2-Iodobenzonitrile, molecular formula is C7H4IN, 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.

methyl 1-(2-cyanophenyl)-1H-imidazole-4-carboxylate A mixture of methyl 1H-imidazole-4-carboxylate (400 mg, 0.003 mol), 2-iodobenzonitrile (800 mg, 0.0035 mol), L-proline (0.073 g, 0.00063 mol), potassium carbonate (0.88 g, 0.0063 mol) and copper(I) iodide (0.060 g, 0.00032 mol) in DMSO (8 mL) was allowed to stir and heated at 90 C. in a sealed tube overnight. The mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to afford methyl 1-(2-cyanophenyl)-1H-imidazole-4-carboxylate. LCMS: (FA)ES+228.1

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

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
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Reference of 5458-84-4, A common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, molecular formula is C7H6INO3, 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.

Example 18; N-{4-[8-(2,4-Dioxo-tetrahydro-pyrimidin-1-yl)-5-methoxy-6-trifluoromethyl-quinolin-3-yl]-phenyl}-methanesulfonamide (I-29); step 1-; A mixture of Cu(I) (10.03 g) and CsF (21.40 g) was finely ground in a mortar while in a glove bag under nitrogen atmosphere to afford a free-flowing powder and transferred to an oven dried 250 mL round bottom flask fitted with a stir bar and septum. The flask was then charged with 2-iodo-5-nitroanisole (15.17 g) and sulfolane (30 mL) and stirred rapidly at 45 C. To the mixture was added dropwise over 4 h using a syringe pump trimethyl(trifluoromethyl)silane (20 mL) and the resulting mixture stirred at RT overnight. The reaction was diluted with EtOAc (500 mL) and stirred in some CELITE 512. The reaction mixture was filtered though a pad of CELITE. The filtrate was diluted to 1 L with EtOAc and washed with 1 L of 10% aqueous NH4OH, 1 L of 1.0M HCl and 500 mL of brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The amber residue was diluted with DCM and purified by flash chromatography (770 g Supelco VersaPak SiO2 column) and eluted with a DCM/hexane gradient (0 to 40% DCM) in 10 column volumes to afford 8.61 g of 82b as a yellow crystalline solid.

The synthetic route of 5458-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; de Vicente Fidalgo, Javier; Li, Jim; Schoenfeld, Ryan Craig; Talamas, Francisco Xavier; Taygerly, Joshua Paul Gergely; US2010/311760; (2010); A1;,
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Reference of 216393-67-8, 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. 216393-67-8, name is 4-Chloro-2-fluoro-6-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows.

4-Chloro-2-fluoro-6-iodoaniline (0.100 g; 0.368 mmol), 4-(3-fluorobenzyl)-N-(4-(triethylsilyl)but-3-ynyl)benzamide (0.145 g; 0.368 mmol), bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.015 g; 0.018 mmol), lithium chloride (0.016 mg; 0.368 mmol) and sodium carbonate (0.078 g; 0.737 mmol) were suspended in DMF (5 mL) and the mixture was stirred at 100 C. for 18 hours. The solution was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 60% ethyl acetate in heptane) to afford 0.102 g (51%) of the title compound as a yellow oil. [0672] ESI/APCI(+): 539 (M+H).

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-2-fluoro-6-iodoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Griffioen, Gerard; Van Dooren, Tom; Rojas De La Parra, Veronica; Allasia, Sara; Marchand, Arnaud; Kilonda, Amuri; Chaltin, Patrick; US2013/274260; (2013); A1;,
Iodide – Wikipedia,
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Application of 51628-12-7, 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 51628-12-7 as follows.

General procedure: A stirred mixture of 4-iodophenylacetonitrile (35), arylboronic acid (36-45) (1.1 equiv), Pd(PPh3)4 (0.03 equiv), KBr (1.1 equiv), and K3PO4 (2.5 equiv) in dioxane (5 mL/mmol) was purged with N2 for10 min at room temperature and then stirred overnight at 85 C under N2. The mixture was diluted with water and extracted with AcOEt. The organic phase was washed three times with water, dried (Na2SO4), and evaporated under vacuum. The residue was chromatographedon silica gel.

According to the analysis of related databases, 51628-12-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ortar, Giorgio; Morera, Enrico; De Petrocellis, Luciano; Ligresti, Alessia; Schiano Moriello, Aniello; Morera, Ludovica; Nalli, Marianna; Ragno, Rino; Pirolli, Adele; Di Marzo, Vincenzo; European Journal of Medicinal Chemistry; vol. 63; (2013); p. 118 – 132;,
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Some common heterocyclic compound, 2142-70-3, name is 1-(2-Iodophenyl)ethanone, molecular formula is C8H7IO, 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. Quality Control of 1-(2-Iodophenyl)ethanone

The operation method of the specific synthesis is the same as that in Example 1, specifically: 1-(2-iodobenzene) ethyl-1-one (1 mmol) and 50 mL of trifluorotoluene are added to the flask,Stir to dissolve 1-(2-iodobenzene) ethyl-1-one in trifluorotoluene, then add 2N HCl (0.5mL),Then, sodium dichromate (0.30g) was added under acidic conditions, heated to 95C and reacted under reflux at this temperature for 6h.After the reaction, spin off the trifluorotoluene in the system, add sodium hydroxide to the water phase to adjust the water phase to pH 9 to remove impurities, and then add hydrochloric acid to the water phase to adjust the water phase to pH 3,After extraction and recrystallization from petroleum ether, the product 2-(2-iodobenzene)-2-glyoxylic acid was obtained with a yield of 86%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2142-70-3, its application will become more common.

Reference:
Patent; Suzhou Aimate Biological Technology Co., Ltd.; Wang Mingzhong; Zhu Mingxin; Su Dao; Li Jinjin; (13 pag.)CN111116358; (2020); A;,
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These common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, 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: C8H7IO

General procedure: 2-Trimethylsilylpyridine (1.2mmol), the aryl halide (1mmol), palladium acetate (0.10mmol), CataXCium A (0.2mmol), CuI (76mg, 0.4mmol) and KF (2.20mmol) were combined in reaction tubes in a Radleys green-house parallel synthesiser under a flow of nitrogen and degassed DMF (1ml) was added. The resulting suspensions were stirred at 90 oC under nitrogen for 12 hours. Reactions were analysed by LC-MS at 1mg/1ml in methanol to determine the yield.

The synthetic route of 1-(3-Iodophenyl)ethanone has been constantly updated, and we look forward to future research findings.

Reference:
Article; Blakemore, David C.; Marples, Louise A.; Tetrahedron Letters; vol. 52; 32; (2011); p. 4192 – 4195;,
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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. 191348-14-8, name is 2-Iodo-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Iodo-4-methoxyaniline

Step D: Preparation of Ethyl 2-(7-Hydroxy-l,2,3,4-tetrahydrocyclopenta[b]indol-3- yl)acetate.2-Iodo-4-methoxyaniline (2.0 g, 8.03 mmol) and ethyl 2-(2-oxocyclopentyl)acetate (2.05 g, 12.1 mmol) were dissolved in DMF (30 mL) and tetraethyl orthosilicate (2.12 g, 10.4 mmol) and pyridinum /7-toluenesulfonate (PPTS) (0.081 g, 0.321 mmol) were added. The reaction mixture was heated and stirred at 135 C for 4 h. After cooling to 120 C, DIEA (3.11 g, 24.09 mmol) and palladium (II) acetate (0.054 g, 0.241 mmol) were added. The reaction mixture was stirred for 3 h and then partitioned between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resultant solution was diluted with 50% ethyl acetate in hexanes and filtered through a pad of silica gel. The filtrate was concentrated and purified by silica gel column chromatography to give 1.9 g of ethyl 2-(7-methoxy-l,2,3,4- tetrahydrocyclopenta[b]indol-3-yl)acetate containing residual ethyl 2-(2-oxocyclopentyl)acetate. The mixture was dissolved in DCM (80 mL) and cooled to 0 C. Boron tribromide (21.0 mL, 21.0 mmol, 1.0 M in DCM) was added and the reaction was stirred for 1.5 h. Ice water was added and the reaction mixture was allowed to reach room temperature. The aqueous mixture was extracted three times with DCM. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (650 mg). LCMS m/z = 260.3 [M+H]+; NMR (400 MHz, CDC13) delta ppm 1.29 (t, J = 7.2 Hz, 3 H), 2.05-2.14 (m, 1H), 2.50 (dd, J= 16.8, 11.2 Hz, 1H), 2.68-2.86 (m, 4H), 3.48-3.58 (m, 1H), 4.16-4.24 (m, 2H), 6.66 (dd, J = 8.6, 2.4 Hz, 1H), 6.85 (d, J= 2.4 Hz, 1H), 7.15 (d, J= 8.7 Hz, 1H), 8.4 (s, 1H).

According to the analysis of related databases, 191348-14-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; MONTALBAN, Antonio, Garrido; BUZARD, Daniel, John; DeMattei, John, Aldo; GHARBAOUI, Tawfik; JOHANNSEN, Stephen, Robert; KRISHNAN, Ashwin, M.; KUHLMAN, Young, Mi; MA, You-An; MARTINELLI, Michael, John; SATO, Suzanne, Michiko; SENGUPTA, Dipanjan; WO2011/94008; (2011); A1;,
Iodide – Wikipedia,
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Synthetic Route of 6828-35-9, 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 6828-35-9 as follows.

1 mmol of 5-chloro-2-iodoaniline, 3 mL of aqueous ammonia at a concentration of 12 mol / L was added to the reaction vessel, 4-methylbenzaldehyde mmol, 0.1 mmol of copper chloride, 0.1 mmol of proline lithium, 1 mmol of sodium hydroxide, 3 mL of water and 1 mL of water. Placed in a microwave reactor at 150 w of power heated to 100 C for 15 min continuous reaction. After completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. The product was purified by column chromatography to give a white solid in 84% yield.

According to the analysis of related databases, 6828-35-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujian Medical University; Ke Fang; Zhang Peng; Xu Jianhua; Wu Wen; Zheng Yu; Wu Lixian; (9 pag.)CN106866543; (2017); A;,
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