Tag: M.W=200-300

Related Products of 52107-68-3,Some common heterocyclic compound, 52107-68-3, name is 5-Iodo-2-methylbenzonitrile, molecular formula is C8H6IN, 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: To a dry flask under N2 atmosphere wasadded anhydrous diglyme (46 mL) and diisopropylamine (5.5 mL, 38.8 mmol). The solution was cooled to -78C in a dry ice bath, then n-butyllithium (2.5 M in hexanes, 5.53 mL) was added slowly. Benzonitrile intermediate 15 (2.4 g, 9.7 mmol) was dissolved in~3mL dry diglyme and added slowly dropwise to the reaction and was allowed to stir at -78C for 60 minutes. Ethyl-3,3-dimethyl acrylate (4.05 mL, 29.1 mmol) was added dropwise and allowed to stir an additional 1 hour at -78C. Concurrently, ZnI2 was generated in situ in a separate flame-dried flaskcontaining dry diglyme (15 mL). After addition of zinc powder (1.59 g, 24.3 mmol) to the flask, iodine (4.92 g, 19.4mmol) was added portionwise over 20 minutes to the reaction (warning:exothermic). The reaction vessel was warmed in 30 second bursts with a heat gun until the color of iodine was replaced with a metallic silver color. The suspension was allowed to cool to room temperature, then added to the first reaction mixture after its 2nd hour of stirring at -78C, and then allowed to slowly warm to room temperature over the course of 2 hours. The reaction was quenched with sat. aq. NH4Cl solution then extracted 3x with diethyl ether. The combined organic extract waswashed 3x with water and 1x with brine, then isolated, dried over MgSO4, vacuum filtered, and concentrated in vacuo. Purification via flash chromatography (0-15% EtOAc:hex) isolated 1.9 g of the desired product; a second flash chromatography purification of impure fractions resulted in an additional 400 mg to combine for 2.3 g of a light yellow solid (63% yield).

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

Reference:
Article; Yestrepsky, Bryan D.; Kretz, Colin A.; Xu, Yuanxi; Holmes, Autumn; Sun, Hongmin; Ginsburg, David; Larsen, Scott D.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1538 – 1544;,
Iodide – Wikipedia,
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Application of 1027513-14-9, 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. 1027513-14-9, name is 1-Fluoro-3-iodo-5-(trifluoromethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

10284] The reaction was carried out according to Scheme1, Step-5, using tert-butyl (Z)-(2-(4-(i-(3-fluoro-i-(tetra-hydro-2H-pyran-2-yl)- 1 H-indazol-5-yl)-2-(4,4,5,5-tetram-ethyl-i ,3,2-dioxaborolan-2-yl)but-i -en-i -yl)-phenoxy) ethyl)carbamate (950 mg, 1.8 mmol) for compound 208 and 1 -fluoro-3-iodo-5-(trifluoromethyl)benzene (523 mg, 1.8 mmol) for compound 209. The crude product was purified by silica gel chromatography (2:8 EtOAc in n-hexane) to give the title compound of Ex. 3, Step-4 (0.5 g, 4 1%).

The synthetic route of 1-Fluoro-3-iodo-5-(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai R&D Management Co., Ltd.; BOCK, Mark; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (141 pag.)US2016/347717; (2016); A1;,
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

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

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

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

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

Synthetic Route of 116632-14-5, 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 116632-14-5 as follows.

8-(3-aminonaphthalen-2-ylthio)-9H-purin-6-amine (S13-4).; A mixture of 8- mercaptoadenine (20.7 mg, 0.124 mmol), neocuproine hydrate (3.9 mg, 0.0185 mmol), Cul (3.5 mg, 0.0185 mmol), sodium tert-butoxide (23.7 mg, 0.24 mmol), S13-3 (100 mg, 0.37 . mmol) and DMF (2 mL) were heated at 115C for 20 h. The solvent was removed under reduced pressure and the residue was purified by preparatory TLC (CH2Cl2:MeOH-NH3 (7N), 10:1) to give 14 mg (37%) of S13-4 as a solid. 1H NMR (500 MHz, CDC^/MeOH-cU) delta 8.18 (s, 1H), 8.12 (s, 1H), 7.71 (d, J= 8.3 Hz, 1H), 7.62 (d, J= 8.1 Hz, 1H), 7.40-7.46 (m, 1H), 7.24-7.30 (m, 1H), 7.20 (s, 1H); MS (ESI) m/z 308.95 [M+H]+.

According to the analysis of related databases, 116632-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; CHIOSIS, Gabriela; TALDONE, Tony; SUN, Weilin; WO2011/44394; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

132554-73-5, name is 2-Fluoro-1-iodo-4-(trifluoromethyl)benzene, 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. SDS of cas: 132554-73-5

To a mixture of the 2-fluoro-1-iodo-4-(trifluoromethyl)benzene(580 mg, 2.0 mmol), tetrakis(triphenylphosphine)palladium(231 mg, 0.2 mmol), and CuI (381 mg, 2.0 mmol) in triethylamine at0 C was added tert-butyldimethyl(2-propynyloxy)silane (341 mg,2.0 mmol). The reaction mixturewas heated to 60 C for 30 min andthen filtrated through a short pad of silica gel. The residue waswashed with dichloromethane and the filtrate concentrated. Thecrude product was then purified by silica gel column chromatography(eluent, petroleum ether) to afford 17 as a brown oil. 1H NMR(400 MHz, CDCl3) delta 7.54 (t, J 7.4 Hz, 1H), 7.35 (dd, J 11.3, 8.9 Hz,2H), 4.58 (s, 2H), 0.92 (d, J 9.8 Hz, 9H), 0.17 (s, 6H).

The synthetic route of 132554-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wei, Hanwen; Mao, Fei; Ni, Shuaishuai; Chen, Feifei; Li, Baoli; Qiu, Xiaoxia; Hu, Linghao; Wang, Manjiong; Zheng, Xinyu; Zhu, Jin; Lan, Lefu; Li, Jian; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 235 – 251;,
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 52914-23-5 as follows. Computed Properties of C8H9IO

EXAMPLE 10 Synthesis of Compound (1B) A mixture of 8.7 g (45 mmol) of 5H-dibenz[b,f]azepine, 12.4 g (50 mmol) of p-iodophenethyl alcohol, 2.8 g (50 mmol) of potassium hydroxide, 4. 8 g (75 mmol) of copper powder, and 20 ml of decalin was heated at an external temperature of 200 C. while stirring in a nitrogen stream for 40 hours. The reaction mixture was cooled nearly to room temperature, chloroform was added thereto, followed by filtration using Celite to remove any insoluble matter. The filtrate was concentrated. To remove decalin, n-hexane was added to the residue, followed by filtration. The filter cake was reprecipitated in methanol, and the resulting crude product was purified by silica gel column chromatography to give 4.2 g (30%) of 5-(4-(2-hydroxyethyl)phenyl)-5H-dibenz[b,f]azepine.

According to the analysis of related databases, 52914-23-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJI PHOTO FILM CO., LTD.; US2003/65171; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com