Month: July 2021

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. COA of Formula: C7H4F3IO

Preparation of intermediate N A solution of tert-butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate (CAS [1041026-70- 3], 500 mg, 2.52 mmol), l-iodo-4-(trifiuoromethoxy)benzene (CAS [103962-05-6], 726 mg, 2.52 mmol), X-phos (240 mg, 0.504 mmol), Pd(dba)2 (145 mg, 0.252 mmol) and t-BuONa (969 mg, 10.1 mmol) in dioxane (8 mL) was irradiated under microwave at 110°C for 1 hour under N2. Water was added to the mixture and the mixture was extracted with ethyl acetate (50 mL x 2). The organic layers were washed brine, dried over MgS04 and filtered. The filtrate was concentrated. The crude product was purified by column chromatography over silica gel (eluent: ethyl acetate/hexane from 0 to 1/5). The desired fractions were collected and concentrated to give N, 500 mg, 50percent.

The synthetic route of 1-Iodo-4-(trifluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; GUILLEMONT, Jerome, Emile, Georges; MOTTE, Magali, Madeleine, Simone; RABOISSON, Pierre, Jean-Marie, Bernard; TAHRI, Abdellah; (194 pag.)WO2017/1660; (2017); A1;,
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Some common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-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. Product Details of 103440-52-4

General procedure: This kind of general experimental procedure is based on our already published procedure.13 The general procedure (GP) was carried out with ortho-iodoester 1a-d (105.0-136.0 mg, 0.40 mmol) and aldehyde 2a-k (195.0-313.0 mg, 1.6 mmol) in the presence of Pd(OAc)2 (5.0 mg, 5 mol%), Ag2O (111.3 mg, 0.48 mmol), and TBHP (257.1 mg, 2.0 mmol) allowing the reaction mixture to stir at 120 C for 12-20 h. Progress of the reaction was monitored by TLC until the ortho-iodoester 1a-d had completely reacted. Then the reaction mixture was removed from the oil bath and allowed to reach r.t. DCE (2 mL) and concd H2SO4 (1.0 mL) were added and the mixture was stirred at 60 C for 5 min to 2 h. Progress of the product formation was monitored by TLC until the reaction was complete. The mixture was quenched by the addition of aq NaHCO3 and then extracted with CH2Cl2 (3 * 15 mL). The combined organic layers were washed with brine, dried (Na2SO4), and filtered. Evaporation of the solvent under reduced pressure and purification of the crude material by silica gel column chromatography (PE/EtOAc) furnished the products 3 (57.0-86.0 mg, 55-69%). The products 3aa, 3ac, 3ai, 3aj, 3ak, 3ba, 3bc, 3be, and 3bj are reported in the literature.9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103440-52-4, its application will become more common.

Reference:
Article; Suchand, Basuli; Satyanarayana, Gedu; Synthesis; vol. 51; 3; (2019); p. 769 – 779;,
Iodide – Wikipedia,
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Synthetic Route of 52548-14-8, 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 52548-14-8 as follows.

In the reactor,Add 90% acetone (volume fraction) 400mL,Stirring,26.2 g of compound (01)Then 34.5 g of potassium carbonate powder was added,0.38 g copper iodide (CuI),1,2,3-triazole.External temperature was raised to 70 ,During the heating process, a large amount of gas is generated,The reaction was stirred at reflux for 5 hours.The reaction mixture was then distilled under reduced pressure at 40 C,When the reaction system is more viscous, add 45mL of water and continue to reduce the steam to distillate without acetone (no acetone in the gas phase). Distilled residue was added 300mL of water, 25% sulfuric acid was added dropwise at room temperature to adjust the pH to 1-2, a yellow suspension.Stir for 30 minutes, filter, and the solids are washed three times with water, 60 mL each. The resulting solid was dried to dryness at 70 C in vacuo,Have pale green solid 19.48g,Compound (1), purity 95.06%.

According to the analysis of related databases, 52548-14-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; He Bifei; Liu Guangyuan; Fan Yuping; (6 pag.)CN104557744; (2017); B;,
Iodide – Wikipedia,
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Reference of 629-09-4, A common heterocyclic compound, 629-09-4, name is 1,6-Diiodohexane, molecular formula is C6H12I2, 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 42-Amino-4-(6-fluorohexyl)-pentane dioic acid a) (2S.4S)-2-tert-Butoxycarbonylamino-4-(6-iodohexyl)-pentane dioic acid dimethyl ester 5.51 g (20 mmol) of Boc-L-Glutamic acid dimethylester (Advanced Chemtech) were dissolved in 60 mL of tetrahydrofuran (THF) and cooled to -70 0C. 44 mL (44 mmol) of 1 M solution of lithium-bis(trimethylsilyl)amide in THF was added drop wise over a period of 1 hour at -70 0C and stirring was continued over 2 h at -70 0C. Then 20.28 g (60 mmol) of 1,6- diiodohexane were added drop wise and, after 2 h at -70 0C, the cooling bath was removed and 100 mL of 2 N hydrochloric acid and 300 mL of ethyl acetate were added. The organic phase was separated, washed neutral with water, dried over sodium sulphate, filtered and the filtrate was reduced in volume by evaporation. The resulting crude product was chromatographed with hexane / ethyl acetate on silica gel. The resulting fractions were combined and reduced in volume by evaporation. Yield: 0.2 g (2.1 %)MS (ESIpos): m/z = 486 [M+H]+1 H NMR (300 MHz, CHLOROFORM-c/) d ppm 1.20-1.70 (m, 29H) 1.75-2.10 (m, 5H) 2.40- 2.50 (m, 1 H) 3.14-3.20 (m, 2H), 3.50-3.75 (m, 3H), 4.15-4.25 (2H) 4.32-4.42 (m, 1H) 5.00- 5.10 (d, 1H)

The synthetic route of 629-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2009/141090; (2009); A1;,
Iodide – Wikipedia,
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Reference of 755027-18-0, These common heterocyclic compound, 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, 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.

A mixture of pyrazole-4-amine dihydrochloride (0.75 g, 4.79 mmol), salicylaldoxime (0.13115 g, 0.96 mmol), cesium carbonate (4.69 g, 14.38 mmol), cuprous oxide (0.06 g, 0.29 mmol), 1-bromo-4-iodo-2-methoxybenzene (1.5 g, 4.79 mmol) and N, N-dimethyl-formamide (5 ml) werecombined in a microwave vial fitted with an N2 inlet and magnetic stir bar. The reaction mixture wasstirred under a nitrogen atmosphere at 90 oc overnight. The solution obtained was allowed to coolto RT, then filtered through celite and the filtrate was concentrated in vacuo. The crude material20 was purified by silica gel chromatography (10% to 60% EtOAc in heptanes) to give 1-(4-bromo-3-methoxyphenyl)-1 H-pyrazol-4-amine (250 mg, MS: 270.2 [M+H+].)

Statistics shows that 1-Bromo-4-iodo-2-methoxybenzene is playing an increasingly important role. we look forward to future research findings about 755027-18-0.

Reference:
Patent; NOVARTIS AG; CHEUNG, Atwood; CHIN, Donovan Noel; DALES, Natalie; FAZAL, Aleem; HURLEY, Timothy Brian; KERRIGAN, John; O’BRIEN, Gary; SHU, Lei; SUN, Robert; SUNG, Moo; WO2014/28459; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 58313-23-8, name is Ethyl-3-iodobenzoate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl-3-iodobenzoate

A 1 L 3 -neck round bottom flask equipped with a 60 mL addition funnel was heated under vacuum with a heat gun. The vacuum line was replaced with a nitrogen line and a thermometer was added. Ethyl 3-iodobenzoate (18.29 ml, 109 mmol) was dissolved in tetrahydrofuran (THF) (362 ml). The mixture was cooled to -20 to -40 0C (dry ice/MeCN, monitored with internal thermometer) and isopropylmagnesium chloride in ether (59.8 ml, 120 mmol) was added dropwise using an addition funnel over 20 minutes. The reaction mixture was then stirred at -20 to -40 0C for 2.5 hours. 3-chlorobenzaldehyde (17.23 ml, 152 mmol) (dissolved in 40 mL of THF) was added over 20 minutes using a clean addition funnel. HPLC and TLC after one hour indicated that the iodide had been consumed. The mixture was warmed to 10 0C and 300 mL 1 N HCl was added carefully through an addition funnel followed by 200 mL of ethyl acetate. The layers were separated and the aqueous layer extracted with 50 mL EtOAc. The combined organic layers was dried over MgSO4, filtered, and concentrated in vacuo. The crude oil was loaded directly onto a column and purified using silica gel chromatography (ISCO: 0-20% ethyl acetate/hexanes (30 min.), 20% (30 min.), 330 g silica) to afford 24.72 g of ethyl 3-[(3- chlorophenyl)(hydroxy)methyl]benzoate (-95% pure, 74% yield). MS (m/z) 290.8 (M+H+).

The synthetic route of 58313-23-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; WO2008/156817; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 2043-57-4,Some common heterocyclic compound, 2043-57-4, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, molecular formula is C8H4F13I, 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.

(2) In another 20 liters of pressure-resistant reactor, 2000 g of perfluorohexylethyl iodide obtained in (1) was added, and the mixture was heated to 125 C with stirring. 6000 g of 4% aqueous dimethylformamide was added to the reactor at a rate of 80 g/min by a metering pump, and the temperature was controlled at 125 to 130 C, the pressure was not higher than 0.35 MPa, and the reaction was continued for 32 hours, and the heating was removed. Neutralize with 2222 g of 11.3% potassium hydroxide aqueous solution, separate the organic phase, and then wash once with 2222 g of deionized water, separate the organic phase, and remove the light component to obtain 1420 g of fluoroalcohol 88% and fluorinated olefin 5.5%. Intermediate product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, its application will become more common.

Reference:
Patent; Jinan Qifu New Materials Co., Ltd.; Shandong Chemical Institute; Li Haijing; Zhang Liting; (6 pag.)CN108911983; (2018); A;,
Iodide – Wikipedia,
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883502-14-5, name is 1-Fluoro-2-iodo-3-methylbenzene, 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: 883502-14-5

Step A: 2-Fluoro-6-methylbenzonitrileA 5 L round bottom flask equipped with adapter, thermocouple and stir bar was charged with DMA (2.4 L) and degassed under vacuum and purged with N2 three times. Tetrakis was added to the mixture (35 g, 30.3 mmol) and the mixture was degassed under vacuum and purged with N2 three times. The reaction was heated to 80C for 30 min. 3-Fluoro-2-iodotoluene (230 g, 974 mmol) and zinc cyanide (68.7 g, 585 mmol) were added and the mixture was degassed under vacuum and purged with N2 three times. The mixture was heated to 80 C for 16 hrs and allowed to cool to RT. The solution was added to 2.0 L aqueous solution of IN NH4OH, which was then extracted three times with 1.5 L EtOAc, washed with 2 L brine, dried over Na2S04, filtered, concentrated and purified by silica chromatography (PE/EA = 10:1) to give thetitle compound.

The synthetic route of 883502-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; TANG, Haifeng; PIO, Barbara; TEUMELSAN, Nardos; PASTERNAK, Alexander; DEJESUS, Reynalda; WO2013/62892; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 52570-33-9, These common heterocyclic compound, 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, 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: Under N2 atmosphere, to a solution of palladium acetate (120 mg, 0.53 mmol, 5 mol %) and XANTPHOS (309 mg, 0.53 mmol, 5 mol %) in anisole (30 mL) was added 3-bromo-5-methyl-pyridin-2-ylamine (5) (2.0 g, 10.7 mmol, 1.0 equiv), aryl iodides (6) (10.7 mmol) and cesium carbonate (4.9 g, 15.0 mmol, 1.4 equiv), and the mixture was stirred at 130 C for 1-13 h. After cooling to room temperature, water (40 mL) was added to the mixture. The mixture was concentrated in vacuo and ethyl acetate (100 mL) was added to the residue. The organic layer was washed with water (20 mL) and concentrated in vacuo to give the crude product, which was purified by flash chromatography to give 7.

The synthetic route of 52570-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mineno, Masahiro; Sera, Misayo; Ueda, Tsuyoshi; Mizuno, Masahiro; Yamano, Mitsuhisa; Mizufune, Hideya; Zanka, Atsuhiko; Tetrahedron; vol. 70; 35; (2014); p. 5550 – 5557;,
Iodide – Wikipedia,
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These common heterocyclic compound, 3718-88-5, name is 3-Iodobenzylamine hydrochloride, 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. SDS of cas: 3718-88-5

Example 41 This example describes the synthesis of N6 -(3-iodobenzyl)-9-[beta-D-ribofuranosyl]-adenine. A mixture of 6-chloropurine riboside (Aldrich Chemical Co., 100 mg, 0.35 mmol), triethylamine (0.146 ml, 1.05 mmol), and 3-iodobenzylamine hydrochloride (103 mg, 0.38 mmol) in ethanol (2 ml) was heated for 18 h at 85 C. in a sealed bottle. After the reaction mixture was concentrated to dryness, the residue was purified on a silica gel column chromatography (CHCl3 –MeOH, 10:1) to yield N6 -(3-iodobenzyl)-9-[beta-D-ribofuranosyl]-adenine (148 mg, 88%) as a colorless solid: m.p. 172 C.; 1 H NMR (DMSO-d6) d 3.54 (m, 1H, H-5’a), 3.67 (m, 1H, H-5’b), 3.96 (d, J=3.3 Hz, 1H, H-4′), 4.14 (m, 1H, H-3′), 4.60 (m, 1H, H-2′), 4.66 (br s, 2H, CH2), 5.16 (d, J=4.4 Hz, 1H, exchangeable with D2 O, 3′-OH), 5.34 (br s, 1H, exchangeable with D2 O, 5′-OH), 5.43 (d, J=6.1 Hz, 1H, exchangeable with D2 O, 2′-OH), 5.89 (d, J=6.0 Hz, 1H, H-1′), 7.11 (pseudo t, J=8.0 and 7.8 Hz, 1H, H-5″), 7.36 (d, J=7.6 Hz, 1H, H-4″ or -6″), 7.58 (d, J=7.8 Hz, 1H, H-4″ or -6″), 7.72 (s, 1H, H-2″), 8.21 (s, 1H, H-2 or 8), 8.40 (s, 1H, H-2 or 8), 8.48 (br s, 1H, exchangeable with D2 O, N6 H,).

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

Reference:
Patent; The United States of America as represented by the Department of Health and Human Services; US5773423; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com