Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 69113-59-3, name is 3-Iodobenzonitrile, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 69113-59-3, category: iodides-buliding-blocks

A mixture of tert-butyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-6-azaspiro[2.5]octane-6-carboxylate (1.50 g, 3.63 mmol), 3-iodobenzonitrile (832 mg, 3.63 mmol), potassium phosphate (2.30 g, 10.89 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (91 mg, 0.103 mmol) in water (3 mL) and dioxane (15 mL) was stirred for 2 h at 80 C under nitrogen atmosphere. The mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by silica gel column chromatography, eluted with petroleum ether/ethyl acetate (1:1) to afford tert-butyl 1-(3′-cyano-[1,1′-biphenyl]-4-yl)-6-azaspiro[2.5]octane-6-carboxylate (1.67 g, 93%) as a white solid. LCMS (ES, m/z): 389 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Forma Therapeutics, Inc.; Martin, Matthew W.; Zablocki, Mary-Margaret; Mente, Scot; Dinsmore, Christopher; Wang, Zhongguo; Zheng, Xiaozhang; (382 pag.)EP3636637; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 124700-41-0,Some common heterocyclic compound, 124700-41-0, name is 2-Fluoro-5-iodobenzoic acid, molecular formula is C7H4FIO2, 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 1C: (3,4-Dihydroisoquinolin-2(lH)-yl)(2-fluoro-5-iodophenyl)methanone[00165] To a suspension of 2-fluoro-5-iodobenzoic acid (Aldrich, 5.27 g, 19.8 mmol) in CH2CI2 (35.0 mL) was added oxalyl chloride (14.9 mL, 29.7 mmol, 1M solution in CH2CI2) followed by 2 drops of DMF via syringe. Gas evolution was initiated and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was then quenched with sat. aq. NH4CI solution and extracted with EtOAc (3 x). The combined organic extracts were dried over Na2S04, filtered and concentrated in vacuo to give crude 2-fluoro-5-iodobenzoyl chloride which was used directly in the next step.[00166] The crude product obtained above was dissolved in CH2CI2 (49.6 mL) and cooled to 0 C. To the solution were added 1,2,3,4-tetrahydroisoquinoline (2.7 mL, 21.8 mmol) followed by 2,6-lutidine (4.6 mL, 39.7 mmol). The resulting reaction mixture was stirred at room temperature for 1 h. The reaction mixture was washed IN HC1 (2 x) and the organic layer was extracted with CH2CI2 (2 x). The combined organic extracts were washed with sat. aq. NaCl solution and dried over a2S04. Filtration and concentration in vacuo provided the title compound (7.55 g, 95%) as a viscous, yellow oil. XH NMR (CDCI3, 1.5: 1 mixture of amide rotamers) delta 7.78-7.66 (m, 2H), 7.26-7.12 (m, 3.5H), 6.98- 6.86 (m, 1.5H), 4.92 (s, 1.5H), 4.50 (br s, 0.5H), 3.65-3.52 (m, 1.5H), 3.04-2.95 (m, 1H), 2.92-2.82 (m, 1.5H); MS(ESI+) m/z 382.1 (M+H)+.

The synthetic route of 124700-41-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BORZILLERI, Robert M.; CAI, Zhen-wei; TEBBEN, Andrew J.; PEREZ, Heidi L.; ZHANG, Liping; SCHROEDER, Gretchen M.; WEI, Donna D.; WO2012/162365; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 260558-15-4,Some common heterocyclic compound, 260558-15-4, name is 4-Bromo-2-iodo-1-methylbenzene, 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.

4-(5-Bromo-2-methyl-phenyl)-6-chloro-pyrimidin-2-ylamine) was synthesised in 2 steps from 5-bromo-2-methyl-1-iodo-benzene as described in Example 81.

The synthetic route of 260558-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cell Therapeutics, Inc.; US2004/204386; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

444-29-1, 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. 444-29-1, name is 1-Iodo-2-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of [9-((1R,2R,4R,5R)-4-ethynyl-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl)purin-6-yl]cyclopentylamine (40 mg, 0.12 mmol), a compound of formula (5), in tetrahydrofuran (4 ml) under nitrogen was added catalytic amounts (3 mg) of dichlorobis(triphenylphosphine)palladium(II) and copper(II)iodide, followed by 1-iodo-2-trifluoromethylbenzene (0.25 ml, 0.3 mmol). Triethylamine (0.4 ml) was then added, and the mixture stirred for 15 minutes at room temperature. The solvent was removed under reduced pressure, and the residue was purified by preparative TLC, eluding with methanol:methylene chloride (6.5:1), to yield [9-((1R,2R,4R,5R)-7,7-dimethyl-4-{2-[2-(trifluoromethyl)-phenyl]ethynyl}-3,6,8-trioxabicyclo[3.3.0]oct-2-yl)purin-6-yl]cyclopentylamine, a compound of formula (6).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Zablocki, Jeff; Palle, Venkata; Elzein, Elfatih; Li, Xiaofen; US2004/43960; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 618-91-7, 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 618-91-7 as follows.

General procedure: A mixture ofmethyl 3-iodobenzoate (1 mmol), corresponding amine (3 mmol), K2CO3(4 mmol), CuI (0.2 mmol) and L-proline (0.4 mmol) in 15 mL of DMSO was heatedat 60 C for 8 h. The cooled mixture was pour into 150 ml water, and extractedwith ethyl acetate (3 × 15 mL), the organic fractions were combined, washedwith saturated brine (2 × 15 ml) prior to drying over anhydrous sodium sulfate.After filtration and concentrate using a rotary evaporator, the residue was purified by silica gel column chromatographyusing a mixture of petroleum ether/ethyl acetate (20 : 1, v/v) as eluent toafford the desired product.

According to the analysis of related databases, 618-91-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Zheng; Pan, Miaobo; Su, Xin; Dai, Yuxuan; Fu, Mian; Cai, Xingguang; Shi, Wei; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 24; 9; (2016); p. 1981 – 1987;,
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. 26670-89-3, name is 2-Bromo-4-iodo-1-methylbenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Bromo-4-iodo-1-methylbenzene

Compound 1 (3 g, 10.10 mmol, 1 eq) in THF (30 mL) was placed into 250 ml round bottom flask. The reaction solution was cooled to -65 C. under a nitrogen atmosphere. n-BuLi (2.2 M, 5.05 mL, 1.1 eq) to the cooled solution was slowly added dropwise, the mixture was stirred for 1 h at the same temperature. TRIMETHYL BORATE (1.26 g, 12.12 mmol, 1.37 mL, 1.2 eq) were added dropwise to the above solution at the same temperature. The mixture was stirred at -65 OC for 1 h. Then cool bath was removed and the mixture was stirred at -65?10 C. for 16 h. The mixture was acidified by dropwise addition of HCl solution (2 M, 5 mL) to the reaction solution, which was stirred for 1.5 hour. The mixture were concentrated in vacuum to afford a residue. The residue was purified by reverse-MPLC (FA condition, A: water, B: MeCN, 40% B). The fraction were concentrated to remove solvent, and aqueous phase was extracted with ethyl acetate (50 mL*3). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate, filtered and the filtrate was concentrated in vacuum to give Compound 2 (1.3 g, 6.05 mmol, 59% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) delta=8.15 (s, 0.5H), 7.95 (s, 0.3H), 7.93 (s, 1H), 7.73 (d, J=7.5 Hz, 1H), 7.66 (d, J=7.5 Hz, 0.3H), 7.37 (d, J=7.5 Hz, 1H), 7.32 (d, J=7.6 Hz, 0.3H), 2.37 (s, 3H), 2.34 (s, 0.9H).

The synthetic route of 26670-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 1ST Biotherapeutics, Inc.; LEE, Jinhwa; KIM, Jae Eun; JO, Suyeon; LEE, Gwibin; LIM, Keonseung; PARK, A Yeong; KIM, Misoon; JUNG, Gyooseung; LIM, Seung Mook; LEE, Minwoo; YANG, Heekyoung; KIM, Hyonam; KIM, Hyeongjun; LI, Wanjun; FAN, Mingzhu; (82 pag.)US2019/100500; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 146137-72-6, 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. 146137-72-6, name is 2-Fluoro-6-iodobenzaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: 3-Iodo-1H-pyrazole-4-carbonitrile (3.62 g, 16.5 mmol) was taken up in dry tetrahydrofuran (67 ml) under nitrogen atmosphere. Sodium hydride (992 mg, 24.8 mmol, 60% in oil) was added in one portion and the mixture was placed in a heated (50 C.) sonication bath for 50 minutes. To this mixture was added 2-fluoro-6-iodobenzaldehyde (5.37 g, 21.5 mmol) and the mixture was placed in an oil bath heated to 60-65 C. After 2 hours stirring additional 2-fluoro-6-iodobenzaldehyde (350 mg, 1.4 mmol) was added and the material was stirred for 1 more hour. The flask was cooled to ambient and close to 90% of the solvent was stripped (rotary evaporator). Diethyl ether (30 ml) and water (50 ml) were added and the mixture was vigorously stirred for 30 minutes. The precipitated product was collected by filtration, rinsing well with diethyl ether and water, and drying in a vacuum oven to provide a light tan powder (4.78 g). This solid product was taken up in a solution of 2% methanol in dichloromethane (about 60 ml, heat to dissolve) and transferred to a reparatory funnel. Water (60 ml) was added and the material was shaken and the organic phase collected. This was dried with magnesium sulfate, filtered and stripped to provide the desired 1-(2-formyl-3-iodo-phenyl)-3-iodo-1H-pyrazole-4-carbonitrile as a light yellow powder (3.973 g). LC/MS calc’d for C11H5I2N3O (m/e) 448.99, obs’d 450 (M+H, ES+).

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

Reference:
Patent; Billedeau, Roland Joseph; Kondru, Rama K.; Lopez-Tapia, Francisco Javier; Lou, Yan; Owens, Timothy D.; Qian, Yimin; So, Sung-Sau; Thakkar, Kshitij C.; Wanner, Jutta; US2012/295885; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-39-4, A common compound: 116632-39-4, name is 5-Bromo-2-iodotoluene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a 20 mL vial with a stir bar was added aryl halide 1 (2.00 mmol), Pd(dba)2 (28.8 mg, 2.5 mol %), Xantphos (28.9 mg, 2.5 mol %). The vial was sealed with a Teflon-lined cap and THF (6.0 mL) was added. The mixture was vacuumed and backfilled with nitrogen (3×). A solution of ethyl 2-bromozincacetate (2a) in THF (0.40 M, 6.0 mL, 1.2 equiv) filtered through a Target Nylon 0.45 mum filter (1.25-inch OD) was syringed in and the reaction mixture was then heated to 65 C and monitored by HPLC. Upon reaction completion based on HPLC analysis (?95% conversion unless the reaction was stalled), the mixture was cooled to room temperature and quenched with 1 M aq HCl (5.0 mL), followed by addition of brine (5.0 mL). The organic layer was separated and concentrated in vacuum. The residue was purified by silica gel column chromatography using gradient EtOAc in hexanes.

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, 5-Bromo-2-iodotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wong, Brian; Linghu, Xin; Crawford, James J.; Drobnick, Joy; Lee, Wendy; Zhang, Haiming; Tetrahedron; vol. 70; 7; (2014); p. 1508 – 1515;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 5876-51-7, 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. 5876-51-7, name is 5-Iodobenzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows.

5.5 Example 5: Synthesis of Compound 1009 (c); Compound 1009 (c) was prepared according to the following scheme. A mixture of Compound 40 (Aldrich Chemical, 2.3 g, 32 mmol), Compound 41 (Aldrich Chemical, 5 g, 26 mmol), HOBT (4 g, 30 mmol), and DCM (200 mL) under argon in a 500 mL-flask was cooled with water and to the mixture was added DIC (4 g, 33 mmol) over about 1 hour. The resulting mixture was stirred at about 25C for about 10 hours. The resultant, filtered solid was removed through filtration and the filtrate was washed with water (100 mL) and aqueous 2N NaOH (40 mL). The organic layer was collected and concentrated under reduced pressure to provide crude Compound 42 (6 g) as brown solid. A mixture of crude Compound 42 (1.5 g, 6 mmol), Compound 43 (available from Oakwood Products Inc., West Columbia, SC; 2 g, 8 mmol), EtOAc (100 mL), TEA (2 mL), (Ph3P) 2PdCl2 (0.2 g, 0.25 mmol), and Cul (200 mg, 1 mmol) in a 250 mL-flask was flushed with argon three times. The reaction mixture was heated to about 50C under argon for about 6 hours. The reaction mixture was concentrated and purified using flash chromatography on a silica gel column of the type described previously in Example 1 eluting with a mixed solvent of 3: 7 EtOAc: hexane to provide 2 g of Compound 44 as a yellow solid (83% yield). The structure of Compound 44 was confirmed by 1H NMR. Compound44 : lHNMR (CDCl3) : o (ppm): 7.11 (dd, J = 1. 5,8. 1Hz, 1H), 6.97 (d, J = 1. 3Hz, 1H), 6.8 (d, J = 8. 1Hz =, 1H), 6.02 (s, 2H), 3.76-3. 79 (m, 2H), 3.64-3. 67 (m, 2H), 3.51-3. 53 (m, 2H), 3.44-3. 46 (m, 2H), 1.47 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 5-Iodobenzo[d][1,3]dioxole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EURO-CELTIQUE S.A.; WO2005/56524; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 13420-63-8,Some common heterocyclic compound, 13420-63-8, name is 2-Chloro-6-iodobenzoic acid, molecular formula is C7H4ClIO2, 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 stirred solution of 2-iodobenzoic acids a (10 mmol) in CH2Cl2, was added DCC (dicyclohexylcarbodiimide, 11 mmol), DMAP (Dimethylaminopyridine, 2 mmol) and alcohols b (10 mmol) in sequence. The resulting solution was stirred overnight at room temperature then filtered through a sand core funnel and washed with diethyl ether (2 x 40mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash column chromatography to obtain the pure product c in moderate to good yields. To a soluton of 2-iodobenzoates c in Et3N (5 mL) was added PdCl2 (PPh3)2 (4 mol %) and CuI (2 mol %) and the reaction vial was flushed with Ar and the reaction mixture was stirred for 5 minutes. A solution of propargyl alcohols d (1.05 equiv) in Et3N (5 mL) were then added dropwise through a syringe for 5 minutes. The resulting solution was stirred at room temperature overnight. When the reaction was considered complete as determined by TLC analysis, the mixture was quenched by addition of saturated aqueous ammonium chloride (10 mL) and extracted with ethyl ether (3 x 40 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by flash column chromatography to give 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-Chloro-6-iodobenzoic acid, its application will become more common.

Reference:
Article; Zhu, Hai-Tao; Tong, Xiao-Juan; Zhou, Ni-Ni; Yang, De-Suo; Fan, Ming-Jin; Tetrahedron Letters; vol. 57; 49; (2016); p. 5497 – 5500;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com