Month: September 2021

Adding a certain compound to certain chemical reactions, such as: 148836-41-3, name is 1-Bromo-4-chloro-2-iodobenzene, 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 148836-41-3, Quality Control of 1-Bromo-4-chloro-2-iodobenzene

Step 2. Ethyl 4-(2-(5-(2-bromo-5-chlorophenyl)pyridin-2-yl)-3-cvclopropylpropanamido) benzoate (9-B) To a round bottom flask was added 9-A from step 1 , l-bromo-4-chloro-2- iodobenzene (66.0 mg, 0.208 mmol), K2CO3 (43.1 mg, 0.312 mmol) and [l ,l’-bis(diphenyl phos- phino)ferrocene]dichloropalladium (15.22 mg, 0.021 mmol) at 13C. The reaction mixture was stirred at 50C for 18 h. The mixture was filtered and concentrated. The residue was purified by preparative TLC (Si02, PE_EtOAc=2: l) to give the title compound. 1H NMR (CDCI3, 400MHz): delta 10.21 (s, 1 H), 8.71 (d, J=2.0 Hz, 1 H), 8.06 (d, J=8.8 Hz, 2 H), 7.76 – 7.88 (m, 2 H), 7.71 (d, J=8.6 Hz, 2 H), 7.43 – 7.50 (m, 2 H), 7.33 (d, J=8.2 Hz, 1 H), 4.41 (q, J=7.1 Hz, 2 H), 3.98 (t, J=7.5 Hz, 1 H), 2.03 – 2.20 (m, 2 H), 1.44 (t, J=7.1 Hz, 2 H), 0.69 – 0.81 (m, 1 H), 0.42 – 0.56 (m, 2 H), 0.19 (dd, J=9.2, 4.5 Hz, 1 H), -0.02 – 0.06 (m, 1 H). MS (ESI) m/z 529.2 (M+H).

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; MERCK SHARP & DOHME CORP.; LIU, Weiguo; EDMONDSON, Scott, D.; GUO, Zhuyan; MERTZ, Eric; OGAWA, Anthony, K.; SO, Sung-Sau; SUN, Wanying; BROCKUNIER, Linda, L.; ALI, Amjad; KUANG, Rongze; WU, Heping; WO2015/183709; (2015); A1;,
Iodide – Wikipedia,
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Application of 41252-96-4, 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. 41252-96-4, name is 2-Chloro-1-iodo-4-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Step A: Preparation of 2-chloro-4-nitro-biphenyl. A mixture of potassium carbonate (1.48 g, 10.7 mmol), phenylboronic acid (645 mg, 5.29 mmol), 3-chloro-4-iodonitro benzene (1.00 g, 3.53 mmol), and THF (31 ml) was degassed with nitrogen in a sealable tube for 10 min. The dichloromethane adduct of 1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (351 mg, 0.429 mmol) was added to the reaction mixture and the pressure tube was sealed. The reaction mixture was stirred at 100 C. for 42 h. The mixture was cooled to 23 C., diluted with DCM (40 ml), and filtered. The filtrate was concentrated. The residue was purified by FCC (3-50% EtOAc/hexanes) to yield the titled compound (796 mg, 97%). 1H NMR (600 MHz, DMSO-d6): 8.42-8.41 (m, 1H), 8.26 (dd, J=8.5, 2.2, Hz 1H), 7.72 (d, J=8.5 Hz, 1H), 7.55-7.48 (m, 5H).

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-1-iodo-4-nitrobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bembenek, Scott D.; Hocutt, Frances M.; Leonard, JR., Barry Eastman; Rabinowitz, Michael H.; Rosen, Mark D.; Tarantino, Kyle T.; Venkatesan, Hariharan; US2010/204226; (2010); A1;,
Iodide – Wikipedia,
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Related Products of 51560-21-5,Some common heterocyclic compound, 51560-21-5, name is 1,4-Diiodo-2,5-dimethoxybenzene, molecular formula is C8H8I2O2, 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: according to the Mizoroki-Heck reaction (Scheme 1). First; by thecoupling between 4-substituted styrenes and dibromo or diiodobenzenes(Method A, Scheme 1), and second; the reaction between4-substituted bromo or iodobenzenes with 1,4-divinylbenzene(Method B, Scheme 1).The general procedure is as follows: 2.05 equivalents of thecorresponding styrene and 1 equivalent of 1,4-dibromo or 1,4-diiodobenzene (Method A, to OPVs 1a-d and 2a-f) or 2.05 equivalentsof the appropriate aryl halide and 1 equivalent of 1,4-divinylbenzene (Method B, to OPVs 1e-h), were placed in a 10 mLheadspace crimp vial equipped with a magnetic stir bar. Then, forboth methods, it was added 0.01 equivalents (1 mol%) of Pd(dba)2,0.1 equivalents (10 mol%) of P(OPh)3 and 5 equivalents of TEA. Thevial was sealed with a PTFE/silicone septum with aluminum capand purged-saturated with N2, then 2 mL of solvent was injected(dry DMF for OPVs-series 1 and 1,4-dioxane for OPVs-series 2,Scheme 1) and the system was purged once again with N2. Thereaction mixture was vigorously stirred at 110 C during 48 h forOPVs-series 1 and 24 h for OPVs-series 2. After finished, highlyfluorescent solid products were obtained.

The synthetic route of 51560-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Estrada, Sandra E.; Ochoa-Puentes, Cristian; Sierra, Cesar A.; Journal of Molecular Structure; vol. 1133; (2017); p. 448 – 457;,
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. 147808-02-4, name is 2-Fluoro-1,4-diiodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: iodides-buliding-blocks

Example 29 5-chloro-N-((1-(3-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (40) A mixture of 2,5-diiodofluorobenzene II-4 (2.50 g, 7.18 mmol), 4-hydroxymethylimidazole hydrochloride (0.967 g, 7.18 mmol), 8-hydroxyquinoline (0.104 g, 0.717 mmol) and K2CO3 (2.00 g, 14.5 mmol) in DMSO (12 mL) was degassed with Ar before being charged with CuI (0.136 g, 0.716 mmol). The mixture in a sealed tube was heated at 130 C. overnight. After being cooled to room temperature, H2O and EtOAc were added. It was filtered through celite. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with MeOH in CH2Cl2 (0-5% MeOH) to give (1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanol (0.39 g).

The synthetic route of 147808-02-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2007/259924; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 54413-93-3, 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. 54413-93-3, name is 2-Iodo-5-methoxybenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: NaIO4 (6.7 g, 31 mmol, 1.0 equiv) and2-iodobenzoic acid (7.4 g, 30 mmol, 1.0 equiv) were suspended in 30% (v:v) aqueousacetic acid (45 mL). The reaction mixture was vigorously stirred and refluxed for 3 hprotecting from light. Cold water (120 mL) was then added and allowed to cool toroom temperature. After 1 h, the crude product was collected by filtration, washedwith ice water (3 x 30 mL) and acetone (3 x 30 mL). After air-drying in the dark,hydroxybenziodoxole 2 was yielded as a white solid.

The synthetic route of 2-Iodo-5-methoxybenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pan, Yue; Jia, Kunfang; Chen, Yali; Chen, Yiyun; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1215 – 1221;,
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

Reference of 1320266-94-1,Some common heterocyclic compound, 1320266-94-1, name is 1-Iodo-3-isopropylimidazo[1,5-a]pyrazin-8-amine, molecular formula is C9H11IN4, 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 -(4-(8-amino-3 -isopropylimidazo[ 1 ,5-a]pyrazin- 1 -yl)phenyl)-3 -(3 – (trifluoromethyl)phenyl)urea (KIRA2). A mixture of compound 1 (22.1 mg, 0.073 mmol), compound 2 (35.5 mg, 0.087 mmol), tetrakis(triphenylphosphine)palladium (2.6 mg, 2.1 muetaiotaomicron) and sodium carbonate (17.0 mg, 0.161 mmol) was dissolved in a 3: 1 mixture of DME/water (280 uL). The mixture was heated overnight at 85 C. The crude mixture was then allowed to cooled to room temperature, diluted in a mixture of acetonitrile/water and purified by reverse phase chromatography (HPLC) to obtain 11.5 mg of KIRA2 (35% yield). TLC (CH2C12:MeOH, 95:5 v/v): Rf = 0.5; 1H NMR (300 MHz, MeOD): delta 7.95 (s, 1H), 7.68-7.64 (m, 1H), 7.65-7.63 (m, 2H), 7.60-7.56 (m, 2H), 7.55-7.48 (m, 2H), 7.34-7.31 (m, 1H), 7.02-7.00 (dd, J = 6.0 Hz, J = 3.0 Hz, 1H), 3.49-3.43 (m, 1H), 1.44 (d, J = 6.0 Hz, 6H); ESI-MS (m/z): [M]+ calcd. for C23H21F3N60, 454.17; [M+l]+ found, 455.5. HPLC Purification Conditions: C18 column (250 x 21 mm), CH3CN/H2 O-0.1% CF3C02H = 1 :99 to 100:0 over 78 min; 8 mL/min; 220 nm and 254 nm detection for 78 min. The purity of GP 1 17 was determined to be >98% by analytical HPLC in two different solvent systems.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-3-isopropylimidazo[1,5-a]pyrazin-8-amine, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; MALY, Dustin J.; BACKES, Bradley, J.; OAKES, Scott, A.; PAPA, Feroz, R.; GHOSH, Rajarshi; WANG, Likun; (220 pag.)WO2016/4254; (2016); A1;,
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

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

Application of 355-43-1,Some common heterocyclic compound, 355-43-1, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane, molecular formula is C6F13I, 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.

-78 CCooled titanium-dichloride(Cp 2 TiCl 2, 59.8 mg, 0.24 mmol) in ether (2.4 mL)To the solution was added i-propyl magnesium chloride (2.0 M in ether solution, 0.24 mL, 0.48 mmol)1,4-Dioxane (46 [mu] L, 0.54 mmol)And n-tridecafluorohexyl iodide (C 6 F 13 I, 78 muL, 0.36 mmol) were charged, then the temperature was adjusted to -50 C. and stirred for 2 hours.Subsequently, benzaldehyde (20 muL, 0.20 mmol) was added, the temperature was raised, and the mixture was stirred at room temperature for 1 hour.After completion of the reaction, 1 N hydrochloric acid was added to terminate the reaction, followed by extraction with ether three times. The organic layers were combined, dried over sodium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 20/1 (v / v)) to obtain 2,2,3,3,4,4,5,5,6, 6,7,7,7-tridecafluoro-1-phenyl-1-hydroxyheptane (85.2 mg, yield:> 99%).

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-6-iodohexane, its application will become more common.

Reference:
Patent; TOKYO INSTITUTE OF TECHNOLOGY; TOSOH F-TECH INCORPORATED; MIKAMI, KOICHI; FUJIU, MOTOHIRO; (46 pag.)JP5894739; (2016); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com