Month: March 2021

2265-91-0, name is 1,3-Difluoro-5-iodobenzene, 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. Application In Synthesis of 1,3-Difluoro-5-iodobenzene

General procedure: In a microwave tube, 425 mg of (S)-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one (Example 1e) are introduced into 1 ml of dimethylformamide, 422 mg of tripotassium phosphate, 380 mg of copper iodide and 2 ml of iodobenzene. The mixture obtained is heated in a microwave oven for 30 minutes at 150 C. The reaction mixture is then centrifuged. The separated supernatant is then rinsed with ethyl acetate and then evaporated to dryness. The residue is taken up with ethyl acetate and the solution obtained is washed with water. The organic phase is separated and then dried over magnesium sulphate, filtered, and concentrated under vacuum. After purification by silica chromatography (gradient of 5% to 15% of the eluent CH2Cl2/MeOH/NH4OH 28% 38/17/2 in dichloromethane), 150 mg of (8S)-2-(morpholin-4-yl)-9-phenyl-8-(trifluoromethyl)-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one are obtained The product is prepared according to the procedure described in Example 12, but using 250 mg of (8S)-2-morpholin-4-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one (Example 1e), 276 mg of 1,3-difluoro-5-iodobenzene, 349 mg of tripotassium phosphate, 156 mg of copper iodide and 93 mg of (1S,2S)-cyclohexane-1,2-diamine. After 1 hour at 150 C. under microwave irradiation and silica column purification of the reaction mixture (elution gradient of CH2Cl2 to CH2Cl2/MeOH 98/02), 91 mg of (8S)-9-(3,5-difluorophenyl)-2-(morpholin-4-yl)-8-(trifluoromethyl)-6,7,8,9-tetra-hydro-4 H-pyrimido[1,2-a]pyrimidin-4-one are obtained in the form of an ochre foam

The synthetic route of 2265-91-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sanofi; Baku, Eritsuku; Bulolo, Morice; Cross, Annie; El Amado, Youssef; Fuiroshiyu, Lom Brunnow; Array, Frank; Carlson, Carl Andreas; Marciniak, Gilbert; Ronan, Baptiste; Shio, Laulan; Bibe, Bertrand; Viviani, Fabrice; Zimerman, Andre; (90 pag.)JP5655070; (2015); B2;,
Iodide – Wikipedia,
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Synthetic Route of 33184-48-4, These common heterocyclic compound, 33184-48-4, name is 4-Chloro-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.

A solution of P(^-Bu)3 (0.0757 M, 5.19 ml_, 0.393 mmol) and a solution of 4-chloro-2-iodo-1-methylbenzene a107 (5.0 g, 19.8 mmol) and tert-butyl acetate (2.53 g, 21.8 mmol) in degassed toluene (50 ml.) are added to a mixture of LiHMDS (7.60 g, 45.5 mmol) and Pd(dba)2 (0.226 g ,0.393 mmol), under argon atmosphere. The reaction mixture is stirred at room temperature for 20 hours (according to the LC-MS data, 2-3 hours are sufficient for the reaction to go to completion) and it is quenched with a saturated ammonium chloride solution (50 mL). After 15 min the organic layer is separated, and the aqueous layer is extracted with diethylether. The combined organic extracts are dried over anhydrous Na2SC>4 and evaporated. The residue is purified by chromatography on silicagel (petroleum ether/AcOEt 10/1 v/v) to afford, after evaporation, tert-butyl (5-chloro-2-methylphenyl)acetate a108 (3.70 g) as a yellow oil (90 % purity). Yield: 77 %.1 H NMR deltaH (CDCI3, 400 MHz, ppm): 1.44 (s, 9H); 2.26 (s, 3H); 3.50 (s, 2H), 7.06-7.19 (m,3H).

Statistics shows that 4-Chloro-2-iodo-1-methylbenzene is playing an increasingly important role. we look forward to future research findings about 33184-48-4.

Reference:
Patent; UCB PHARMA S.A.; WO2008/132139; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 170112-66-0, The chemical industry reduces the impact on the environment during synthesis 170112-66-0, name is 3,4,5-Trifluoroiodobenzene, I believe this compound will play a more active role in future production and life.

3,4,5-fluoro-iodobenzene (10.0g, 38.0mmol), bromo difluoroethyl acetate (23.1g, 114mmol) and copper (2.90g, 45.6mmol) and stirred for 3 h with dimethyl sulfoxide solution (40ml) 80 of.Ethyl acetate was added to the reaction mixture, the insoluble matter was separated by filtration.Pour the water filtrate was extracted with ethyl acetate.The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The concentrate was purified by silica gel column chromatography and purified by (elution solvent ethyl acetate / n-hexane = 1/10) to give the title compound as a colorless oil (yield 7.20 g, 75% yield).

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, 3,4,5-Trifluoroiodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hokko Chemical Industry; Suzuki, Jun; Hiroki, Eisho; Nonaka, Hisato; (15 pag.)JP2016/84346; (2016); A;,
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 58313-23-8 as follows. Recommanded Product: 58313-23-8

B. 3-iodobenzohydrazideIn a schlenck tube, a mixture of ethyl 3-iodobenzoate (1.8Og, 6.52mmol) and hidrazine hydrate (3.18ml, 65.2mmol) in ethanol (25ml) was heated at 8O0C overnight. The solvent was evaporated and the crude redissolved in DCM and washed with water and brine. The organic layer was dried, filtered and concentrated under vacuum to give the title compound as a white solid (88% yield).ESI/MS (m/e, %): 263 [(M+1)+, 100]

According to the analysis of related databases, 58313-23-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6293-83-0, name is 2-Iodo-4-nitroaniline, 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. COA of Formula: C6H5IN2O2

General procedure: In a typical reaction, PdCl2(PPh3)2 (88 mg, 0.125 mmol), CuI (24 mg, 0.125 mmol) and THF (5 ml) were placed in an oven-dried, 2-neck RB flask. To this suspension, 2-iodoaniline (5.47 mg, 2.5 mmol) and triethylamine (702 mul, 5.0 mmol) were added. The reaction mixture was degassed by bubbling with argon for 15 min. Phenylacetylene (300 mul, 2.75 mmol) was then added, and the reaction mixture stirred at RT. After complete consumption of the 2-iodoanilines (~2 h, by TLC), the reaction mixture was filtered through celite, and the solvent rotary evaporated to obtain the crude product which was purified by silica gel (60-120 mesh) column chromatography using ethylacetate/ hexane (1:9, v/v) as eluent to give pure 2-phenylethynylaniline, 2a (400 mg, 83%).

The synthetic route of 6293-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 55; 40; (2014); p. 5495 – 5498;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 501433-06-3, These common heterocyclic compound, 501433-06-3, name is 2,3-Difluoro-1,4-diiodobenzene, 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.

1,2-difluoro-3,6-diiodobenzene (7.3 g, 20.0 mmol), Compound 45 (12.8 g, 42.0 mmol), a 2 M aqueous solution of Na2CO3 (40 mL, 80.0 mmol), DME (40 mL), toluene (40 mL), and Pd[PPh3]4 (1.2 g, 1.0 mmol) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 8 hours. After the completion of the reaction, the resultant was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (100 mL) was charged into the funnel. Then, the mixture was extracted with CH2Cl2. The extract was dried with MgSO4, and was then filtered and concentrated. The resultant sample was purified by silica gel column chromatography, whereby a white solid was obtained in an amount of 8.2 g in 65% yield-FD-MS analysis C44H32F2O2: theoretical value 630, observed value 630

Statistics shows that 2,3-Difluoro-1,4-diiodobenzene is playing an increasingly important role. we look forward to future research findings about 501433-06-3.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2301926; (2011); 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. 689260-53-5, name is 2-Bromo-5-iodo-1,3-dimethylbenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8BrI

A flask charged with a stir bar, 2-bromo-5-iodo-1 ,3-dimethyl-benzene (1 .0 g), bis- (pinacolato)-diboron (1 .0 g), potassium acetate (1 .1 g) and dimethyl sulfoxide (10 ml_) is purged with argon for 5 min. [1 ,1 ‘-Bis(diphenylphosphino)-ferrocene]- dichloropalladium(ll) (0.26 g) is added at room temperature, and the mixture is stirred at 90 C for 3 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (MgSO4) and concentrated. The residue is chromatographed on reversed phase (HPLC; acetonitrile/water) to give the title compound . LC (method 9): tR = 1 .30 min; Mass spectrum (ESI+): m/z = 31 1/313 (Br) [M+H]+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144097; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 181765-86-6, A common heterocyclic compound, 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, molecular formula is C8H6BrIO2, 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 1-a] was synthesized according to Scheme 1 below.Methyl 5-bromo-2-iodobenzoate (25.0 g, 73 mmol) in a 500 mL round bottom flask reactorAdd 4-dibenzofuranboronic acid (18.7g, 88mmol), tetrakis (triphenylphosphine) palladium (1.7g, 0.15mmol), potassium carbonate (20.2 g, 146.7mmol), 125mL toluene, 125mL tetrahydrofuran 50 mL of water was added thereto.The temperature of the reactor was raised to 80 degrees and stirred for 10 hours. After the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated.The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain Intermediate 1-a (75.0 g, 60.1%).

The synthetic route of 181765-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC Ltd.; Cha Sun-uk; Jeong Gyeong-seok; Song Ju-man; Lee Yu-rim; Park Sang-u; Kim Hui-dae; Park Seok-bae; (65 pag.)KR2019/111856; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 116632-39-4, name is 5-Bromo-2-iodotoluene, molecular formula is C7H6BrI, 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. category: iodides-buliding-blocks

Apparatus set-up: (0305) A 5 L 3 -necked round-bottomed flask, equipped with a mechanical overhead stirrer, reflux condenser, nitrogen inlet and exhaust. (0306) Experimental Procedure: (0307) Intermediate 3 (128 g, 0.435 mol) and intermediate 4 (128.8 g, 0.435 mol) were taken in toluene (1 L) and ethanol (1 L). (0308) Sodium carbonate solution (161.3 g, 1.522 mol, dissolved in 500 mL of water) was added. (0309) The reaction mixture was degassed with nitrogen for an hour. (0310) PdCl2 (PPh3)2 (15.2 g, 0.021 mol) was added and heated at 80 C for 18 h. (0311) After completion of the reaction, the mixture was filtered through a Florosil-silica plug and concentrated. (0312) The residue was dissolved in ethyl acetate (2 L), washed with water (1 L), brine (1 L), dried over sodium sulphate and concentrated. (0313) The crude product (159 g) was purified by silica column chromatography using 5 to 6 % ethyl acetate in hexane as an eluent to get 65 g of Intermediate B with 81 % HPLC purity. It was again purified by reverse phase column chromatography (in 5 g per run) using water/ acetonitrile as an eluent to get 35.6 g of Intermediate B. (0314) The material was dissolved in dichloromethane (500 mL), heated to 45 C, filtered the hot solution and concentrated to get 35 g of Intermediate B with 99.64 % HPLC purity as viscous oil. (0315) ^-NMR (400 MHz, COCh): delta [ppm] 2.29 (s, 3H), 7.19 (d, = 8.0 Hz, 1H), 7.37 – 7.42 (m, 3H), 7.47 – 7.52 (m, 2H), 7.61 (d, / = 8.4 Hz, 2H), 7.86 (s, 1H), 7.96 (d, = 7.6 Hz, (0316) 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 116632-39-4, its application will become more common.

Reference:
Patent; CAMBRIDGE DISPLAY TECHNOLOGY LIMITED; SUMITOMO CHEMICAL CO., LTD; HUMPHRIES, Martin; TARRAN, William; KAMTEKAR, Kiran; STACKHOUSE, Philip; LEE, James; (76 pag.)WO2017/153731; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 5876-51-7,Some common heterocyclic compound, 5876-51-7, name is 5-Iodobenzo[d][1,3]dioxole, molecular formula is C7H5IO2, 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.

[00230] To 27.7 mg PdCl2(dppf).CH2Cl2 in a reaction tube under nitrogen were added 4 ml dioxane, 0.14 ml (1.0 mmol) of 2,6-dimethylpiperidine, 0.23 ml (1.5 mmol) pinacolborane (crimson solution) and 261 mg (1.05 mmol) 1-iodo-3,4-methylenedioxybenzene. The crimson reaction solution was warmed to 80 C. with stirring in an oil bath. Analysis of the reaction solution by gc, as described above, was carried out at intervals (see Table 19.1). The reaction is fast and is complete after 4 h reaction time. The initial reaction rate with 1 mmol of 2,6-dimethylpiperidine as base exceeds that found using 3 mmol of triethylamine (see Table 17.3; catalyst not activated prior to reaction) and the final product distribution is essentially the same. This is not the case if one compares the reactions in which either 1 mmol of 2,6-dimethylpiperidine or 1 mmol of triethylamine is used as base. As noted above, dehalogenation in reactions using 1 mmol of triethylamine is considerable (23% of peak area in the gc is due to 1,3-benzodioxole) and the desired product, the pinacol ester of 3,4-methylenedioxyphenylboronic acid is only 69% of peak area. [00231] The results are different when 3 mmol of 2,6-dimethylpiperidine is used in the reaction. The reaction rate is reduced, especially after the first 1 to 2 hours (see Table 19.2). The results suggest that in situ catalyst activation may be initially enhanced using 2,6-dimethylpiperidine but excess of this base also retards the reaction. Dehalogenation occurs predominantly during the earlier part of the reaction. [TABLE-US-00007] TABLE 19.1 Rate of product formation on reaction of 1-iodo-3,4-methylenedioxybenzene with pinacolborane at 80 C., catalyst PdCl2(dppf).CH2Cl2, base 2,6-dimethylpiperidine (1.0 mmol). The concentrations are expressed in area % (uncorrected for response factors) determined by gc analysis of aliquots of the reaction solution taken at selected reaction times*. Reaction Time (h) [C00047] [C00048] [C00049] [C00050] 1 8.7 2 70 20 2 8.4 4.3 42 44 3 8.5 6.2 16 67 4 11.5 6.5 0.3 80 5 11.6 6.4 0 80 *The reaction was quenched at the selected reaction time by addition of the aliquot of reaction solution to a water/ethyl acetate mixture. [TABLE-US-00008] TABLE 19.2 Rate of product formation on reaction of 1-iodo-3,4-methylenedioxybenzene with pinacolborane at 80 C., catalyst PdCl2(dppf).CH2Cl2, base 2,6-dimethylpiperidine (3.0 mmol). The concentrations are expressed in area % (uncorrected for response factors) determined by gc analysis of aliquots of the reaction solution taken at selected reaction times*. Reaction Time (h) [C00051] [C00052] [C00053] [C00054] 1 8.9 1.3 69 20 2 9.2 2.8 49 38 3 9.6 3.5 33 53 4 11 5.1 25 58 5 10 5.6 18 66 6 10 5.9 13 71 25.5 12 6.1 2.2 78 *The reaction was quenched at the selected reaction time by addition of the aliquot of reaction solution to a water/ethyl acetate mixture.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Iodobenzo[d][1,3]dioxole, its application will become more common.

Reference:
Patent; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com