Month: May 2021

Synthetic Route of 14192-12-2,Some common heterocyclic compound, 14192-12-2, name is 2,5-Diiodobenzoic acid, molecular formula is C7H4I2O2, 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 : A RBF equipped with a reflux condenser was charged with 4-bromophenol (15.5 g, 89.4 mmol), 2,5-diiodobenzoic acid (25.700 g, 68.7 mmol), EtOAc (0.337 ml, 3.44 mmol), and toluene (100 mL). Cs2C03 (44.8 g, 137 mmol) was carefully added portion- wise. After stirring at RT for 1 min, the mixture was heated to 50 C for 40 min and then heated to 100 C for 20 hrs. The reaction mixture was allowed to cool to RT. The mixture was filtered through Celite and the solids were washed with EtOAc. The filtrate was diluted with water (200 mL), acidified with 2N HC1 (300 mL), and extracted with EtOAc (4 x 500 mL). The organic extract was washed with brine and dried over sodium sulfate. The organic fraction was concentrated under reduced pressure to afford crude 2-(4-bromophenoxy)-5-iodobenzoic acid (31.1 g) as a tan oil that solidified upon standing.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Diiodobenzoic acid, its application will become more common.

Reference:
Patent; AMGEN INC.; WHITE, Ryan; CHENG, Yuan; MINATTI, Ana Elena; YANG, Bryant; ZHENG, Xiao Mei; LOPEZ, Patricia; HUMAN, Jason B.; EPSTEIN, Oleg; JUDD, Ted; SHAM, Kelvin; XUE, Qiufen; WO2013/44092; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1031929-20-0, name is 4-Fluoro-2-iodobenzonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Fluoro-2-iodobenzonitrile

To a solution of 1 (30mg, 0.157mmol), 2 (78mg, 0.315mmol) and Cs2CO3 (256mg, 0.785mmol) in DMF (2mL) were added 1 mg of Pd(dba)2 and 1 mg of Xantphos. The suspension was degassed under vacuum and purged with N2 several times. The mixture was stirred at 120 C for 1hr. The reaction was quenched by adding water and extracted with EA. The combine organic phases were washed by water, brine, dried over anhydrous Na2S04 and concentrated to dryness. The residue was purified by pre-TLC to obtain the title compound Compound 204 (5.15mg, yield: 10.5%). LCMS: m/z, 310.1(M+H)+; 1HNMR (d-CDCl-3, 400MHz): delta 8.55-8.57 (m, 1H), 7.64-7.68 (m, 1H), 7.45-7.48 (m, 1H), 7.38-7.42 (m, 1H), 7.24-7.28 (m, 1H), 6.39-6.44 (m, 1H), 6.24-6.28 (m, 1H), 4.12-4.20 (m, 1H), 4.03-4.09 (m, 1H), 3.70-3.82 (m, 2H), 2.60-2.69 (m, 1H), 2.35-2.53 (m, 1H).

The synthetic route of 1031929-20-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; BALDWIN, John J.; WU, Chengde; SHEN, Chunli; WO2014/124560; (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. 914636-20-7, name is 4-Iodo-3-(trifluoromethyl)benzoic acid, A new synthetic method of this compound is introduced below., SDS of cas: 914636-20-7

A mixture of 4-iodo-3-(trifluoromethyl)benzoic acid (2.00 g, 0.0063287 mol), Cu(I)CN (1.70 g, 0.018986 mol), PPh3 (2.49 g, 0.009493 mol), and 40 mL of dry DMF was heated at 100 ± 5C for 14 h. After the end of the reaction was established by TLC, the reaction mixture was partitioned in ethyl acetate and water, and extracted the water layer with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. Product was purified by a silica gel column using hexane and ethyl acetate (4:1 to 3:1 and then 2:1) as eluent to afford 1.10 g (85%) of the titled compound as light brown solid.1H NMR (400 MHz, DMSO-d6) d 14.02 (br s, 1H, OH), 8.39-8.32 (m, 2H, ArH), 7.41-7.31 (m, 1H, ArH).Mass (ESI, Negative):213.91 [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; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane, D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (202 pag.)WO2019/222556; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 136618-42-3, name is Benzyl 4-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C14H11IO2

Intermediate 2: Phenylmethyl 4-(4-amino-6-methyl-1/-/-indazol-1-yl)benzoate; 6-Methyl-1 H-indazol-4-amine (5.48g, 37.3mmol), copper (I) iodide (71 mg, 0.37mmol), frans-i ^-cyclohexanediamine (420mg, 0.37mrnol) 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; 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; WO2009/50220; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 51738-07-9, 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. 51738-07-9, name is 2-Chloro-6-iodobenzaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a flame-dried 100 mL round-bottom flask NaHMDS (2 mmol, 1 eq) in THF (5 mL) were addedand the solution was cooled down to 0 C. A solution of the corresponding benzyl phosphonate(II) (2 mmol, 1 eq) in THF (12 mL) was added dropwise under stirring. The reaction was stirred fora further 10 min at 0 C, then a solution of the haloaldehyde (I) (2 mmol, 1 eq) in THF (4 mL) wasadded dropwise. The mixture was allowed to warm from 0 C to room temperature 12-14 h understirring. The reaction mixture was quenched with water (10 mL). The aq layer was extracted withEt2O (3 x 10 mL). The combined organic layers were washed with 10% aq NaHSO3 (2 x 5 mL)and then with brine (10 mL). The combined organic layers were dried over Na2SO4 andconcentrated by evaporation in vacuo to give 10a-c. (10a: E/Z: 10:1, 10b: E, 10c: E/Z: 20:1). TheE-isomers of compounds 10a?-c? was obtained using column chromatography (2.0% EtOAc inpetroleum ether) from mixtures of 10a-c. The E/Z ratio was determined by 1H NMR.

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

Reference:
Article; Roehrig, Ute F.; Majjigapu, Somi Reddy; Caldelari, Daniela; Dilek, Nahzli; Reichenbach, Patrick; Ascencao, Kelly; Irving, Melita; Coukos, George; Vogel, Pierre; Zoete, Vincent; Michielin, Olivier; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4330 – 4333;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 1189352-83-7, A common heterocyclic compound, 1189352-83-7, name is 3-Chloro-5-iodobenzotrifluoride, molecular formula is C7H3ClF3I, 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 6Preparation of 1 -[3-chloro-5-(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone A tetrahydrofuran solution of isopropylmagnesium chloride (2 M, 36.0 mL, 71.8 mmol) was added dropwise to a solution of l-chloro-3-iodo-5-(trifluoromethyl)benzene (i.e. the product of Example 5) (20.0 g, 65.3 mmol) in tetrahydrofuran (30 mL) at -5 0C. The mixture was stirred for 1 h at 0-5 0C. Methyl trifluoroacetate (10.0 g, 78.1 mmol) was added dropwise to the mixture while maintaining the temperature 0-5 0C. When the addition was complete the mixture was stirred for 90 min.Hydrochloric acid (1 N, 100 mL) was added dropwise to the mixture at 0-5 0C. When the addition was complete the mixture was extracted with ether (2 x 100 mL).The combined extracts were dried and evaporated. The oil was dissolved in toluene (55 mL), and /?-toluenesulfonic acid monohydrate (0.100 g, 0.525 mmol) was added to the mixture. The mixture was boiled for 30 min, and the water/toluene methanol/toluene azeotropes were removed by distillation at atmospheric pressure. The distillation was continued at reduced pressure to give the product as an oil (12.4 g, 69% yield), b.p. 93- 103 0C at 6.7 kPa. 1H NMR (CDCl3) 8.21-8.19 (m, 2H), 7.95 (s, IH).

The synthetic route of 1189352-83-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2009/126668; (2009); A2;,
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. 128651-99-0, name is 6-Iodochroman-2-one, A new synthetic method of this compound is introduced below., Product Details of 128651-99-0

In a flame dried and argon flushed Schlenk flask 2.00 g6-iodochroman-2-one (16, 7.30 mmol, 1.00 eq) was suspendedin 140 cm3 MeOH. H2SO4 (1.95 cm3) was added tothis colorless suspension. The suspension dissolved and thecolorless solution was warmed to 55 C and stirredovernight at this temperature. After full conversion (24 h)was detected by GC-MS, the brown solution was neutralizedby addition of 50 cm3 saturated NaHCO3 solution andthe solvent was removed in vacuo. The brown residue wasdiluted with 100 cm3 H2O, and extracted with DCM(3 9 100 cm3). The combined organic layers were driedover MgSO4, filtered and concentrated in vacuo. The crudeproduct was purified via flash column chromatography(cyclohexane/EtOAc = 5/1, Rf = 0.18, UV and CAM) and1.70 g (76 %) 17 were isolated as a light yellow oil.1H NMR (300 MHz, CDCl3): d = 7.39-7.35 (m, 3H, HAr,OH), 6.65-6.62 (m, 1H, HAr), 3.66 (s, 3H, CH3), 2.82 (t,J = 5.9 Hz, 2H, CH2), 2.69 (t, J = 5.9 Hz, 2H, CH2) ppm;13C NMR (76 MHz, CDCl3, APT): d = 176.2 (Cq, CO),154.6 (Cq, CAr), 139.2 (CAr), 137.0 (CAr), 130.4 (Cq, CAr),119.9 (CAr), 82.9 (Cq, CAr), 52.6 (CH3), 35.0 (CH2), 24.5(CH2) ppm; GC-MS (EI, 70 eV; MT_50_S): tR = 6.92 -min; m/z (%) = 306 (17) [M?], 274 (100) [M?-OCH3],246 (64) [M?-C2H3O2], 91 (0.31) [M?-C4H7O2I]; TLC:Rf = 0.18 (cyclohexane/EtOAc = 5/1, UV and CAM);HRMS (EI): m/z calcd for [M?] 305.9753, found 305.9766.

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:
Article; Trobe, Melanie; Breinbauer, Rolf; Monatshefte fur Chemie; vol. 147; 3; (2016); p. 509 – 521;,
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. 229178-74-9, name is 2,6-Difluoro-3-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H3F2IO2

To a mixture of 2,6-difluoro-3-iodobenzoic acid 3 (2.84 g, 10.0 mmol) in methanol (30 mL) was added SOCl2 (0.1 mL) dropwise at 0 C. After being stirred at reflux for 3 h, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 15:1 to 10:1, v/v) to give the desired compound 4 as a white solid (2.75 g, 92%): mp 54-55 C (lit.6 mp 53-55 C); 1H NMR (CDCl3) delta 3.95 (s, 3H, CH3), 6.78-6.82 (t, 1H, J = 8.4 Hz, ArH), 7.78-7.83 (m, 1H, ArH); 13C NMR (CDCl3) delta 53.10, 75.42, 75.46, 75.69, 75.73 (dd, JC-F = 4.2, inlMMLBox = 26.8 Hz), 111.49, 111.69, 111.89 (t, JC-F = 19.8 Hz), 113.81, 113.84, 114.03, 114.07 (dd, JC-F = 3.9, inlMMLBox = 22.4 Hz), 141.42, 141.45, 141.51, 141.54 (dd, JC-F = 3.1, inlMMLBox = 9.4 Hz), 157.99, 158.05, 160.52, 160.58 (dd, JC-F = 6.2, inlMMLBox = 252.6 Hz), 159.48, 159.53, 162.04, 162.09 (dd, JC-F = 5.1, inlMMLBox = 256.2 Hz), 161.16; GC-MS: 298 M+.

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 229178-74-9.

Reference:
Article; He, Qiu-Qin; Gu, Shuang-Xi; Liu, Jia; Wu, Hai-Qiu; Zhang, Xuan; Yang, Liu-Meng; Zheng, Yong-Tang; Chen, Fen-Er; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 5039 – 5045;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 957193-64-5, The chemical industry reduces the impact on the environment during synthesis 957193-64-5, name is 7-Iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one, I believe this compound will play a more active role in future production and life.

C) 7-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one Under nitrogen atmosphere, to a solution of 7-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one (12.5 g) in a mixed solvent of N,N-dimethylformamide (200 mL) and dimethyl sulfoxide (600 mL) was slowly added 1 M potassium 1,1,1,3,3,3-hexamethyldisilazane/tetrahydrofuran solution (63.6 mL) under ice-cooling. The reaction mixture was stirred at 0C for 30 min, and [2-(chloromethoxy)ethyl](trimethyl)silane (11.3 mL) was slowly added thereto at the same temperature. The reaction mixture was stirred at room temperature for 2 hr, and the solvent was evaporated under reduced pressure. To the residue was added aqueous sodium carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/ethyl acetate) to give the title compound (6.86 g). 1H NMR (400 MHz, DMSO-d6) delta 0.01 (9H, s), 0.90 (2H, t, J = 7.6 Hz), 3.59 (2H, t, J = 8.0 Hz), 4.07 (2H, d, J = 1.6 Hz), 5.31 (2H, s), 7.55 (1H, d, J = 1.6 Hz), 7.92 (1H, d, J = 2.0 Hz).

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, 7-Iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; MIKAMI, Satoshi; NAKAMURA, Shinji; ASHIZAWA, Tomoko; SASAKI, Shigekazu; TANIGUCHI, Takahiko; NOMURA, Izumi; KAWASAKI, Masanori; EP2848618; (2015); 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. 141738-80-9, name is 3-Chloro-4-iodobenzotrifluoride, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

Step A: Diboron pinacol ester (329.61mg, 1.30mmol, 1.10eq) and tetrakis(triphenylphosphine)platinum(73.53mg, 59.09umol, 0.05eq) were added to a solution of compound 10 (200.00mg, 1.18mmol, 1.00eq) in 2-methyltetrahydrofuran(5.00mL), the reaction solution was purged three times with nitrogen and stirred at 70C under nitrogenatmosphere for 5 hours. After the reaction solution was cooled to 0C, compound 5 (285.58mg, 945.27umol, 0.80eq),cesium carbonate (769.97mg, 2.36mmol, 2.00eq), 0.4mL water, 5mL 2-methyltetrahydrofuran and dichlorobis(triphenylphosphine)palladium (41.47mg, 59.08umol, 0.05eq) were added, then the reaction solution was purged three timeswith nitrogen and stirred at 20C under nitrogen atmosphere for 12 hours. Then 2-chloro-4-trifluoromethyl iodobenzene(717.09mg, 2.34mmol, 2.00eq), aqueous potassium hydroxide (4M, 1.46mL, 5.00eq), dichlorobis(triphenylphosphine)palladium (41.06mg, 58.50umol, 0.05eq) and 10mL 2-methyltetrahydrofuran were added to the reaction solution,which was subsequently purged three times with nitrogen. After stirring at 70C under nitrogen atmosphere for 12 hours,the reaction solution was filtered through celite, concentrated and purified by silica gel column chromatography(PE:EA=40:1 to 15:1) to give the compound 47 as a yellow jelly (738.00mg), which was directly used in the next step.

The synthetic route of 141738-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Luoxin Biotechnology (Shanghai) Co., Ltd.; Shandong Luoxin Pharmaceutical Group Stock Co., Ltd.; LU, Jianyu; DING, Charles Z.; HU, Lihong; HE, Huijun; CHEN, Shuhui; DONG, Jiaqiang; WANG, Tie-lin; (124 pag.)EP3434668; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com