Tag: M.W=200-300

68507-19-7, name is 3-Iodo-4-methoxybenzoic acid, 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. Product Details of 68507-19-7

Methyl 3-iodo-4-methoxybenzoate (29.2 g, 0.1 mol) was suspended in EtOH (150 mL), the solution of NaOH (4.4 g, 0.11 mol) was added in one portion. The mixture was stirred and heated at 40C overnight, then cooled, diluted with water (400 mL). 3-Iodo-4-methoxybenzoic acid was precipitated with conc. HCl, filtered off, washed with cold water, and dried over P4O10. The acid was suspended in CHCl3 (150 mL), and SOCl2 (9.5 mL, 0.13 mmol) was added. The mixture was stirred overnight, then evaporated and the residue was distilled under reduced pressure to give the desired acid chloride as a solid (mp ca. 50C, bp 145-150C/1 Torr). Yield 18.2 g (61%).

The synthetic route of 68507-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OXFORD GENE TECHNOLOGY IP LIMITED; EP1506959; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 138385-59-8, A common heterocyclic compound, 138385-59-8, name is 4-Iodo-2,6-dimethylaniline hydrochloride, molecular formula is C8H11ClIN, 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 2 L round bottom flask was charged 4-iodo-2,6-dimethylbenzenamine hydrochloride salt (55 g, 194 mmol), methyl 2-(benzyloxycarbonyl)acrylate (59.2 g, 252 mmol), tetrabutylammonium chloride (59.2 g, 213 mmol), palladium (II) acetate (4.34 g, 19.4 mmol), and tetrahydrofuran (1.2 L, degassed by a flow of nitrogen for 30 min). The mixture was stirred so that a suspension was formed and then degassed by a flow of nitrogen for 30 min. Triethylamine (10 mL, 789 mmol) was added and the resulting mixture was heated at reflux for 3 h. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, washed with tetrahydrofuran (2¡Á100 mL), and concentrated. The residue was dissolved in dichloromethane, washed with water (3¡Á) and brine (2¡Á), dried over sodium sulfate, and concentrated. Flash chromatography (silica gel using 1:9 ethyl acetate/dichloromethane) gave a tan solid. The solid was recrystallized from warm methanol (210 mL) and water (100 mL). The mixture was held at room temperature overnight, then at 0 C. for 2 h, and finally at -15 C. for 2 h. The resulting solid was filtered, washed with ice cold 1:1 methanol/water, and dried under high vacuum overnight to give 44.7 g (65%) as a light tan solid which was a mixture of Z/E isomers (73:27). 1H-NMR (DMSO-d6) 6, 2.05 (s, 6H), 3.61 (s, 0.8H), 3.68 (s, 2.2H), 5.00 (s, 0.54H), 5.13 (s, 1.46H), 5.24 (s, 2H), 7.40-7.21 (m, 8H), 8.51 (s, 0.27H), 8.79 (s, 0.73H); 13C-NMR (DMSO-d6) delta 17.8, 51.7, 65.3, 119.4, 120.0, 120.3, 127.3, 127.7, 128.3, 130.9, 135.8, 137.2, 146.9, 154.7, 166.0.

The synthetic route of 138385-59-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chaturvedula, Prasad V.; Han, Xiaojan; Jiang, Xiang-Jun J.; US2006/122250; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 3930-83-4, A common heterocyclic compound, 3930-83-4, name is 2-Iodobenzamide, molecular formula is C7H6INO, 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.

General procedure: To a 10 mL reaction tube were added MCM-41-L-Proline-CuBr(135 mg, 0.1 mmol), 2-halobenzamide 1 (1.0 mmol), benzylamine derivative 2 (2.0 mmol), K2CO3 (3.0 mmol), and DMSO (3 mL). The reaction mixture was stirred at 110 or 120 C under air for 6-12 h.After being cooled to room temperature, the reaction mixture was diluted with 20 mL of EtOAc, and filtered. The MCM-41-L-Proline-CuBr complex was washed with distilled water (2 5 mL) and ethanol (2 5 mL), and reused in the next run. The filtrate was washed with water (2 10 mL) and dried over MgSO4. After being concentrated in vacuo, the residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc 3:1 to 2:1)to afford the target product 3.

The synthetic route of 3930-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yan, Nan; You, Chongren; Cai, Mingzhong; Journal of Organometallic Chemistry; vol. 897; (2019); p. 161 – 169;,
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. 39959-51-8, name is (2-Iodophenyl)methanamine, A new synthetic method of this compound is introduced below., SDS of cas: 39959-51-8

Example 14 N4-[(trans-4-aminocyclohexyl)methyl]-N2-{2-[(2-aminophenyl)thio]benzyl}-5-nitropyrimidine-2,4-diamine To a solution of {4-[(2-chloro-5-nitro-pyrimidin-4-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester (100 mg, 0.26 mmol) in a mixture of CH2Cl2 (2 mL) and DMF (1 mL) were added 2-iodobenzylamine (192 mg, 0.82 mmol) and DIPEA (135 muL, 1.04 mmol). The reaction mixture was stirred at room temperature for 16 h and concentrated in vacuo. The resulting residue was diluted with EtOAc and washed with water (*3) and then with brine. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel preparative TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 97 mg (64%) of (4-{[2-(2-iodo-benzylamino)-5-nitro-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester.

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 Pharmaceuticals, Inc.; US2006/25433; (2006); 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. 59528-27-7, name is (4-Iodophenyl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

10 g of 2-(2-propynyloxy) tetrahydropyran (1 equiv. 71.36 mmol) was added to a solution of 5.1g sodium azide (1.1 equiv, 78.5 mmol), 1.41 g sodium ascorbate (0.1 equiv, 7.14 mmol), 2.29 ml trans-N-N?-dimethylcyclohexane-1,2-diamine (0.25 equiv, 17.83 mmol), 3.4 g copper(I)-iodide (0.025 equiv, 17.83 mmol) in 75 ml methanol. To this mixture 19.97 g of 4 iodobenzylamide HCl was added. The reaction was stirred overnight at 55 C. The solvent was removed under reduced pressure. The crude reaction was purified by liquid chromatography with dichloromethane:ultra (22% MeOH in DCM with 3% NH4OH) mixture 0% to 40% on silica gel. The product was then reacted with alginate as described below.

The synthetic route of 59528-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vegas, Arturo J.; Veiseh, Omid; Doloff, Joshua C.; Ma, Minglin; Tam, Hok Hei; Bratlie, Kaitlin; Li, Jie; Bader, Andrew R.; Langan, Erin; Olejnik, Karsten; Fenton, Patrick; Kang, Jeon Woong; Hollister-Locke, Jennifer; Bochenek, Matthew A.; Chiu, Alan; Siebert, Sean; Tang, Katherine; Jhunjhunwala, Siddharth; Aresta-Dasilva, Stephanie; Dholakia, Nimit; Thakrar, Raj; Vietti, Thema; Chen, Michael; Cohen, Josh; Siniakowicz, Karolina; Qi, Meirigeng; McGarrigle, James; Lyle, Stephen; Harlan, David M.; Greiner, Dale L.; Oberholzer, Jose; Weir, Gordon C; Langer, Robert; Anderson, Daniel G.; Nature Biotechnology; vol. 34; 3; (2016); p. 345 – 352;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2265-92-1, name is 1,4-Difluoro-2-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. Quality Control of 1,4-Difluoro-2-iodobenzene

To a solution of 1 (15mg, 0.079mmol), 2 (38mg, 0.158mmol) and Cs2CO3 (128mg, 0.395mmol) in DMF (lmL) were added 2 mg of Pd(dba)2 and 2 mg of Xantphos. The suspension was degassed under vacuum and purged with N2 several times. The mixture was stirred at 120 C for lh. LCMS showed the SM was consumed completely. Then the reaction mixture was diluted with EA (10mL) and washed with brine (2mL) twice. The organic solution was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified by p-TLC to give the desired compound Compound 219 (4mg, yield: 16.6%). LCMS: m/z, 303.1 (M+H)+; 1HNMR:(d-CDCl3, 400MHz): delta 8.55(d, J=4.8, 1H), 7.61~7.65(m, 1H), 7.44(d, J=7.6, 1H), 7.19~7.25(m, 1H), 6.81~6.88(m, 1H), 7.25~7.32(m, 2H), 3.83~4.05(m, 2H), 3.46~3.60(m, 2H), 2.33~2.63(m, 2H).

The synthetic route of 2265-92-1 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

Adding a certain compound to certain chemical reactions, such as: 645-00-1, name is 1-Iodo-3-nitrobenzene, 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 645-00-1, category: iodides-buliding-blocks

General procedure: An aryl halide (1.0mmol) and a terminal alkyne (1.0mmol) was added to a mixture of PS-triazine-Pd(II) (0.001mmol) and base (1mmol) in a glass flask under vigorous stirring. The mixture was stirred at room temperature for 3h under aerobic conditions. Upon completion of the reaction, the reaction mixture was dissolved in chloroform (2mL). The palladium catalyst was separated from the mixture by filtration, washed with acetonitrile (10mL), and reused in the next run. Then to the chloroform solution was added toluene (1.0mmol) as the internal standard for GC analysis. After the analysis, the solvent was removed under vacuum, and the crude product was subjected to silica gel column chromatography using CHCl3-CH3OH (95:5) as eluent to afford the pure product.

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:
Article; Bakherad, Mohammad; Bahramian, Bahram; Jajarmi, Saeideh; Journal of Organometallic Chemistry; vol. 749; (2014); p. 405 – 409;,
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. 52807-27-9, name is 4-Chloro-2-iodoanisole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6ClIO

Example 5: Synthesis of 1-BICYCLO [2.2. 1] hept-5-en-2-ylmethyl-4- (5-chloro-2-methoxy-phenyl)-2-methyl-piperazine. CH3 Pd2dba3 1 I N (+)-BINAP OMe CNH NaBH (OAc) 3 OMe N I C 3 18-crown-6 SN QCH3 y’J”3 i J N NaOt-Bu/THF H pwave, 80 OC 5 mine [0102] 10 mg (0. 010 eq) PD2DBA3-CHC13, 9. 0 mg (0.015 eq) racemic BINAP, 135 mg (1.4 eq) NAOT-BU, 370 mg (1.4 eq) 18- crown-6 ether and 1.0 mL anhydrous tetrahydrofuran were combined in a microwave vial. 268 mg (1.0 EQ, 1. 0 mmol) 4-Chloro-2- IODOANISOLE was added, followed by 120 mg (1.2 eq) racemic 2- methylpiperazine. The vial was flushed with nitrogen prior to being microwaved at 80C for 5 minutes. The reaction mixture was diluted with 1.0 mL DMSO: methanol (1 : 1) and centrifuged (4, 000 rpm, RT, 8 min). The supernatant was filtered and purified by reverse-phase HPLC (2-99% CH3CN in 0. 085% TFA (AQ), 50 ML/MIN, 2.0 mL injected). Yield = 50 mg (14%) of a light brown oil (isolated as the mono-TFA salt); [0103] 1H-NMR (400 MHZ, DMSO-D6) No. 9.14 (br d, J = 8.6 Hz, 1H), 8. 71 (br d, J = 7.8 HZ, 1H), 7. 10 (dd, J = 8.7 HZ, 2. 4 HZ, 1H), 6. 99 (d, J = 8.8 HZ, 1H), 6. 94 (d, J = 2.5 HZ/1H)/3. 80 (S, 3H), 3. 42 (br M, 4H), 3. 17 (M, 1H), 2. 85 (M, 1H), 2. 72 (M, 1H), 1. 25 (d, J = 6.4 HZ, 3H) ; LC/MS retention time (10-99% CH3CN/0. 05% TFA gradient over 5 min): 1.82 min; Theoretical (M+H) + m/z = 241. 1; Found 241.2.

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 52807-27-9.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2005/30188; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 612-55-5, name is 2-Iodonaphthalene, molecular formula is C10H7I, 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. SDS of cas: 612-55-5

Substrate Compound 1 (0.1 mmol, 43.4 mg) , Pd(TFA)2 (0.01 mmol, 3.3 mg) , and Ag2C03 (0.15 mmol, 41.4 mg) were weighed out open to air and placed in a microwave tube (5 mL) with a magnetic stir bar. The aryl iodide (0.15 mmol), 2-picoline (0.02 mmol, 2 muIota , TFA (0.02 mmol, 2 mu) , and DCE (0.5 mL) were added. The reaction vessel was sealed and the mixture was first stirred at room temperature for 10 minutes and then heated to 100 C for 20 hours with vigorous stirring. Upon completion, the reaction mixture was cooled to room temperature. The solvents were removed under reduced pressure and the resulting mixture was purified by a silica gel-packed flash chromatography column using toluene/EtOAc or hexane/EtOAc as the eluent. (S) -3- (Naphthalen-2-yl) -2-phthalimido-N- (2,3,5,6- tetra luoro-4- (trifluoromethyl)phenyl) propanamide (2q) Substrate Compound 1 was arylated following the general arylation procedure A. Analysis of crude reaction mixture by 1H NMR showed a 14:1 ratio of mono- and diarylated products. After purification by column chromatography using toluene/EtOAc (30/1) as the eluent, Compound 2q was obtained as a light yellow solid (50.7 mg, 91%). NMR (600 MHz, CDC13) delta 8.52 (br s, 1H) , 7.77-7.71 (m, 4H) , 7.68-7.62 (m, 4H) , 7.41-7.37 (m, 2H) , 7.36-7.34 (m, 1H) , 5.47 (dd, Ji = 6.6 Hz, J2 = 10.2 Hz, 1H) , 3.82-3.74 (m, 2H) ; 13C NMR (150 MHz, CDC13) 6168.1, 166.7, 134.6, 133.3, 132.9, 132.5, 131.0, 128.7, 127.9, 127.6, 127.5, 126.5, 126.2, 125.9, 123.8, 56.3, 35.4; HRMS (ESI- TOF) Calcd for C28Hi6F7N203 [M+H] + : 561.1044; found: 561.1048.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 612-55-5, its application will become more common.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; YU, Jin-Quan; WO2015/131100; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products 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.

Alternatively, to a mixture of magnesium (1.46 g, 60.0 mmol) and tetrahydrofuran (100 ml) was added a small crystal of iodine followed by 4-chloro-2-iodo-toluene (12.62 g, 50 mmol). The mixture was heated under gentle reflux in an argon atmosphere for 6 hours and then cooled to -78 C. A solution of cyanuric chloride (7.84 g, 42.5 mmol) in tetrahydrofuran (45 ml) was added over 25 minutes. After stirring at -78 C. for 1 hour, the mixture was slowly warmed to room temperature and stirred for 16 hours. The reaction mixture, cooled in an ice bath, was quenched by slow addition of hydrochloric acid (1 M, 15 ml). The mixture was diluted with water (150 ml) and extracted with dichloromethane (3*125 ml). The combined extracts was washed with water (150 ml), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluding with ethyl acetate-hexane (7:93) to provide 2,4-dichloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazine (10.2 g, 87% yield) as a white powder.

The synthetic route of 33184-48-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cell Therapeutics, Inc.; US2003/153570; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com