Category: iodides-buliding-blocks

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 627-32-7 name is 3-Iodo-1-propanol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 627-32-7

Mitragynine (50.0 mg, 0.126 mmol) was dissolved in 3-iodopropanol (0.33 mL), and acetonitrile (CH3CN, 0.5 mL) was added to the solution. Under ice cooling, IBDA (40.5 mg, 0.126 mmol) was added in four portions at intervals of 4 minutes, and the mixture was stirred at room temperature for 1 hour in an argon atmosphere. The reaction liquid was poured into an ice-cold saturated sodium bicarbonate aqueous solution and extracted three times with ether. The extracted organic layers were washed with brine and dried over sodium sulfate, followed by evaporation of the solvent under reduced pressure and vacuum drying. Thus, a residue was obtained. The resultant residue was purified by medium pressure liquid chromatography (aminosilica gel, 30% ethyl acetate/n-hexane) to obtain an iodinated form represented by the following formula (V) (31.9 mg, 46% yield).Analysis data of the product are shown below. 1H-NMR (400 MHz, CDCl3) delta [ppm]: 7.45 (1H, s, H-17), 7.32 (1H, dd, J=8.0, 8.0 Hz, H-11), 7.24 (1H, d, J=7.6 Hz, H-12), 6.75 (1H, d, J=8.1 Hz, H-10), 3.87 (3H, s, 9-OCH3), 3.81 (3H, s, 17-OCH3), 3.71 (3H, s, 22-OCH3), 3.29 (2H, m, H2-1?), 3.05-2.98 (3H, overlapped, H-3, H-5, and H-15), 2.93 (2H, dd, J=5.3, 5.3 Hz, H2-3?), 2.89-2.70 (3H, overlapped, H-6, H-14, and H-21), 2.59 (1H, m, H-5), 2.45 (1H, dd, J=11.2, 2.6 Hz, H-21), 2.08-1.88 (3H, overlapped, H-14 and H2-2?), 1.74-1.56 (3H, overlapped, H-6, H-19, and H-20), 1.23 (1H, m, H-19), 0.82 (3H, dd, J=7.2, 7.2 Hz, H3-18).13C-NMR (100 MHz, CDCl3) delta [ppm]: 184.0 (C-2), 169.3 (C-22), 160.7 (C-17), 156.5 (C-9), 155.5 (C-13), 130.9 (C-11), 123.0 (C-8), 114.3 (C-12), 111.2 (C-16), 108.8 (C-10), 86.1 (C-7), 63.2 (C-1?), 62.2 (17-OCH3), 61.8 (C-3), 58.1 (C-21), 55.4 (9-OCH3), 51.3 (22-OCH3), 50.3 (C-5), 40.5 (C-20), 39.3 (C-15), 35.2 (C-6), 33.7 (C-2?), 25.9 (C-14), 18.9 (C-19), 12.8 (C-18), 3.7 (C-3?).UV (MeOH) lambdamax: 301.0, 245.5 (sh), 221.5 nm.CD (0.151 mM, MeOH, 24 C.), lambda nm (De): 345 (0), 309 (+2.8), 290 (0), 281 (-0.8), 275 (0), 258 (+4.8), 242 (0), 221 (-9.4), 210 (0). EI-MS (%) m/z: 582 (M+, 41), 397 (100).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodo-1-propanol, and friends who are interested can also refer to it.

Reference:
Patent; NATIONAL UNIVERSITY CORPORATION CHIBA UNIVERSITY; TAKAYAMA, Hiromitsu; (11 pag.)US2016/340352; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

13194-68-8, A common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, 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 solution of NCTD (1, 1.0 g, 5.95 mmol) dissolved in tetrahydrofuran (THF, 10 mL)accompanied by triethylamine (TEA, 0.5 mL) as the acid-binding agent was added the correspondingaromatic amine (1 equiv., 5.95 mmol). When the reaction was complete after 14 h as checkedby TLC analysis, the solution was concentrated under reduced pressure and diluted with acetone(100 mL). The resulting filter cake was either recrystallized from methanol or purified by columnchromatography (MeOH/CH2Cl2, 1: 4, v/v) to afford the desired products II (1-36). The yields,physical properties, 1H-NMR, 13C-NMR, and HRMS-ESI of the target compounds II were as follows.

The synthetic route of 13194-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yang; Sun, Wenbo; Zha, Shunqing; Wang, Huan; Zhang, Yalin; McPhee, Derek J.; Molecules; vol. 20; 12; (2015); p. 21464 – 21480;,
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. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 64248-58-4

General procedure: General procedure for the synthesis of alpha-arylacetic acid tert-butyl esters: A Schlenk tube was charged with aryl iodide (1.0mmol), CuI (9.5mg, 0.05mmol), 2-picolinic acid (12mg, 0.10mmol), and cesium carbonate (978mg, 3.0mmol). The tube was evacuated and backfilled with argon three times before tert-butyl acetoacetate (2.0mmol) and 2mL of 1,4-dioxane was added. The tube was immersed in an oil bath, and the reaction mixture was stirred at the indicated temperatures for 33-48h. The cooled mixture was partitioned between ethyl acetate and saturated NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with PE/EA=20:1 to 3:1) to provide the desired alpha-arylacetic acid tert-butyl esters.

The synthetic route of 64248-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Conference Paper; Zhao, Duo; Jiang, Yongwen; Ma, Dawei; Tetrahedron; vol. 70; 20; (2014); p. 3327 – 3332;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 452-68-6, name is 1-Fluoro-4-iodo-2-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. 452-68-6

To a dry 25 ml flask fitted with nitrogeninlet/outlet was addedK3PO4 (0.589 g), ethylene glycol (0.178 g), 2-fluoro-5-iodotoluene (0.368 g), copper(l) iodide (0.028 g) and Example28 (0.516 g). To this was added previously degassed anhydrous propan-2-ol (10ml). This was then subjected to a nitrogen/vacuum cycle. The reaction was then heated to reflux for 17.5 hours under a nitrogen atmosphere. After this time the reaction was filtered, and the liquors poured into water (50ml). This was then extracted with DCM (1 x 30 ml and 2 x 20ml), the organic layers combined and washed with 1 M ammonia solution (1 x 100 ml) then 1M ammonia solution (1 x 50ml) and water (1 x 50ml). The organics were dried over sodium sulfate and concentrated to dryness under reduced pressure. The residue was thencolumned over silica (30 g) using DCM/EtOAc as eluent. This afforded 0.140 g of the title compound.8H (DMSO-d6) 8.74(1H, s), 7.78-7. 75 (1H, d, J 9.7 Hz), 7.65- 7.61 (3H, m), 7.58-7. 51 (2H, m), 7.02-6. 96 (1H, t), 6.82-6. 79 (1H, m), 6.76- 6.72 (1 H, m), 6.53-6. 49 (1 H, d, J 9.7 Hz), 4.63-4. 60 (1 H, t), 3.89 (1 H, broad), 3.28-3. 21 (3H, m), 2.80-2. 78 (1H, m), 2.14 (3H, s), 1.71-1. 51 (4H, m). LCMS ES+ RT 3.29 min, 478.0 (M+H)+.

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 452-68-6.

Reference:
Patent; CELLTECH R & D LIMITED; WO2004/113349; (2004); A1;,
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. 612-55-5

General procedure: An aryl iodide (2′: 0.20 mmol) in a 20 mL Schlenk tube was added successively toluene (1.5 mL), a THF solution of an arylmagnesium bromide (1: 0.30 mmol) and THF (overall 0.50 mL), and the resulting mixture was stirred at 80 C for 24 h. After cooling, the reaction mixture was quenched with a 1 N HCl aqueous solution (1.0 mL) and extracted with Et2O (10 mL x 3). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was subjected to silica gel chromatography (hexane orhexane/diethyl ether, PTLC) to give the corresponding coupling product (3).

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:
Article; Shirakawa, Eiji; Okura, Keisho; Uchiyama, Nanase; Murakami, Takuya; Hayashi, Tamio; Chemistry Letters; vol. 43; 6; (2014); p. 922 – 924;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

82998-57-0, Name is 3-Iodo-4-methylbenzoic acid, 82998-57-0, 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.

Example 52; 3-r8-r2,6-difluorophenvn-2-r4-methyl-L4′-birhoirhoeridin-l’-v?-7-oxo-7,8- dihvdropyridor2,3-ff1pyrimidin-4-yll-4-methylbenzoic acidTo a stirring solution of 3-iodo-4-methylbenzoic acid (60 g, 0.22 mol, 1 eq) in degassed DMF (1400 mL, 23.3 vol.) was charged 4,4,4′,4′,5,5,5′,5′-octamethyl- 2,2′-bi-l ,3,2-dioxaborolane (81.4 g, 0.32 mol, 1.4 eq) followed by potassium acetate (112 g, 1.14 mole, 5eq) and [l,r-bis(diphenylphosphino)ferrocene]- dichloropalladium(II) (18.7 g, 0.02 mole, 0.1 eq). The resulting mixture was placed under a nitrogen atmosphere and was heated to 80 0C with the exclusion of light overnight. The mixture was then concentrated under high vacuum and the residue partitioned between EtOAc and 2M HCl. The mixture was then filtered and the layers separated. The aqueous phase was re-extracted with EtOAc. The combined EPO organics were then washed with brine, dried and evaporated to yield a brown solid that was applied to a silica plug then eluted with 2:1 cyclohexane : ethyl acetate. Fractions were then combined and evaporated to yield a brown foam that was triturated with cyclohexane, collected by filtration then dried in vacuo to yield A- methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoic acid, delta (CDCl3) 8.50- 8.49 (IH, d), 8.04-8.02 (IH, dd), 7.27-7.25 (IH, d), 2.61 (3H, s), 1.36 (12H, s).To the compound 4-chloro-8-(2,6-difluorophenyl)-2-(4-methyl-l,4′- bipiperidin-r-yl)pyrido[2,3-?f|pyrimidin-7(8H)-one (47.5 mg, 0.1 mmol) in dioxane (3 niL) and water (1 mL) were added 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)benzoic acid (38.4 mg, 0.15 mol), potassium carbonate (83 mg, 0.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (4.6 mL, 0.005 mmol). The mixture was heated with microwave at about 1500C for about 15 min. The mixture was concentrated & then mixed with DMSO (0.75 mL) and water (0.25 mL). Separation by EtaPLC afforded the title compound (39 mg, 68%). LC-MS m/z 574 (M+Eta)+.

Statistics shows that 3-Iodo-4-methylbenzoic acid is playing an increasingly important role. we look forward to future research findings about 82998-57-0.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/104917; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2401-21-0, 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. 2401-21-0, name is 1,2-Dichloro-3-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 12 2-Amino-5-chloro-N-cyclohexyl-N-methyl-3-trifluoromethyl-benzylamine and its hydrochloride by method B A solution of 9.5 gm of 2-amino-N-cyclohexyl-N-methyl-3-trifluoromethyl-benzylamine and 3 ml of pyridine in 40 ml of tetrahydrofuran was cooled to -10¡ã C, and while stirring at this temperature it was admixed in the course of 20 minutes with a solution of 9.1 gm of iodobenzene dichloride in 80 ml of tetrahydrofuran. After stirring it for 4.5 hours at 0¡ã to -10¡ã C, the mixture was allowed to stand for 18 hours at 20¡ã C. Thereafter, the reaction mixture was diluted with water and extracted with chloroform. The organic phase was washed with aqueous potassium carbonate and water, and after drying it over magnesium sulfate, the solution was evaporated in vacuo, and the oily residue, the free base 2-amino-5-chloro-N-cyclohexyl-N-methyl-3-trifluoromethyl-benzylamine, was taken up in ethyl acetate. The hydrochloride of the base was precipitated from this solution with isopropanolic hydrochloric acid. After recrystallizing the salt three times from ethanol in the presence of charcoal, colorless crystals were obtained which had a melting point of 260¡ã-262¡ã C.

The synthetic route of 1,2-Dichloro-3-iodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim GmbH; US4101671; (1978); A;,
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. 124700-41-0, name is 2-Fluoro-5-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., 124700-41-0

Preparation 2 PNU-244020 Ethyl 3-(2-fluoro-5-iodophenyl)-3-oxopropanoate To a solution of 2-fluoro-5-iodobenzoic acid (4.03 g, 15.14 mmol) in 11 mL freshly distilled THF is added CDl (2.96 g, 18.24 mmol) in small portions. Vigorous gas evolution is observed. The reaction is stirred overnight. In a separate flask, ethyl malonate potassium salt (2.84 g, 16.69 mmol) is suspended in 10 mL CH3CN. To this solution is added chlorotrimethylsilane (2.15 mL, 16.94 mmol) and the reaction is stirred at room temperature overnight. The latter reaction is cooled to 0 C. and DBU (5.00 mL, 33.43 mmol) is added dropwise. This reaction is stirred at 0 C. for 3 h. The solution of the CDI adduct is then cannulated over and the mixture is stirred at 0 C. for 2 h. Upon complete conversion to product as evidenced by TLC, the solution is quenched with water and 6N HCl (8 mL). The reaction is partitioned with diethyl ether. The organic layer is washed with 1N HCl and then brine, dried over Na2SO4, filtered, and concentrated to give a light orange oil. The oil is dissolved in EtOAc and adsorbed onto silica. Purification by chromatography (eluent 3% EtOAc/hexanes) affords the desired product as a colorless oil which crystallized upon standing (2.51 g, 7.46 mmol, 49%). Physical characteristics are as follows: m.p. 54-56 C.; 1H NMR (300 MHz, CDCl3) delta 12.67, 8.18, 7.70, 6.89, 5.54, 4.28, 1.35; IR (drift) 2984, 1627, 1558, 1476, 1422, 1390, 1358, 1292, 1262, 1221, 1201, 1071, 1028, 823, 807 cm -1; MS (EI) m/z 336 (M+), 336, 249, 122, 107, 94, 86, 84, 69, 68, 51; Anal. Calcd for C11H10FIO3: C, 39.31; H, 3.00; Found: C, 39.35; H, 2.92.

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; Vaillancourt, Valerie A.; Larsen, Scott D.; Nair, Sajiv K.; US2002/42397; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

56096-89-0, 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 56096-89-0 as follows.

In a MW tube was added 4-fluoro-2-iodobenzoic acid (600 mg, 1.88 mmol), 1 H-1 ,2,3- Triazole (0.22 ml_, 3.76 mmol) and (1 R,2R)-N 1 ,N2-dimethylcyclohexane-1 ,2-diamine (0.06 ml_, 0.38 mmol). To these solids were added 1 ,4-Dioxane (2 ml_) and Water (0.2 ml_), then Cul (18 mg, 0.09 mmol) and finally Cs2C03 (1 .22 g, 3.76 mmol). The mixture was then warmed to 100 C for 2.5 hrs and left at RT O/N . HCI 6 N was added until pH 2, then volatiles were removed under vacuum and the crude material was purified by RP on C18 column (from H20/CH3CN 95:5 + 0.1 % of FA to H20/CH3CN 5:95 + 0.1 % of FA) affording 4-fluoro-2-(2H-1 ,2,3-triazol-2-yl)benzoic acid (p185, 250 mg, y= 64%) as white solid. MS (m/z): 206.3 [M-H]”

According to the analysis of related databases, 4-Fluoro-2-iodobenzoic acid, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); 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. 83863-33-6, name is 5-Iodo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., 83863-33-6

Step A N-(5-iodo-2-methylphenyl)iminodiacetic acid diethyl ester Using 5-iodo-2-methylaniline (4.66 g, 20 mmol) and according to the method of Reference Example 61, step C, the title compound (8.31 g, yield>100%) was obtained as a pale-yellow oil. 1H-NMR (400 MHz, DMSO-d6); delta(ppm) 1.15 (t, J=7.1, 6H), 2.20 (s, 3H), 3.98 (s, 4H), 4.06 (q, J=7.1, 4H), 6.93 (d, J=8.0, 1H), 7.28 (dd, J=7.9, 1.5, 1H), 7.39 (d, J=1.4, 1H).

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; MITSUBISHI TANABE PHARMA CORPORATION; US2012/196824; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com