Tag: M.W=200-300

Some common heterocyclic compound, 847685-01-2, name is 4,5-Difluoro-2-iodoaniline, molecular formula is C6H4F2IN, 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. name: 4,5-Difluoro-2-iodoaniline

A dark violet solution of 2-iodo-4,5-difluoroaniline (1a) (148 mg, 0.582 mmol), gold complex [AuPPh3NN] 2 (308 mg, 0.5 mmol),[Pd(PPh3)4] (52 mg, 0.045 mmol) in 7 ml of acetonitrile were stirred in an argon atmosphere at 60-65 C for 1 h. The reaction mixture was evaporated. The product was isolated by column chromatography on SiO2, using a mixture of methylenechloride with ethylacetate (3:1) as the eluent. Yield: 71 mg (50%), dark purple crystals, Tmelt = 140-141 C. UV spectrum(CH2Cl2), lambdamax, nm (lgepsilon): 240 (4.00), 260 (3.79), 346 (4.07), 578 (2.88). IR spectrum (KBr), v , cm-1: 3357, 3168 (NH2), 2996(C-H), 1646, 1592, 1502, 1355, 1143, 873, 788. Found, %: 55.07, 5.63, N 14.64. Calculated, %: 54.93, 5.63, N14.78.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 847685-01-2, its application will become more common.

Reference:
Article; Tretyakov; Makhneva; Politanskaya; Bagryanskaya, I. Yu.; Stass; Journal of Structural Chemistry; vol. 59; 3; (2018); p. 689 – 696; Zh. Strukt. Kim.; vol. 59; 3; (2018); p. 712 – 719,8;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 103962-05-6,Some common heterocyclic compound, 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, molecular formula is C7H4F3IO, 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.

To a 250 mL reaction flask was added 3-bromo-1H-1,2,4-triazole (5 g, 33.8 mmol), CuI (0.644 g, 3.38 mmol) and Cs2CO3 (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with nitrogen gas, and then DMSO (33.8 ml) and 1-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100° C. for 20 hours (h). The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite®. The Celite® was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash column chromatography using EtOAc/hexanes as eluent to yield the title compound (3.78 g, 73percent): mp 69-70° C.; 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H), 7.70 (d, J=8.9 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H); 19F NMR (376 MHz, CDCl3) delta ?58.04; EIMS m/z 307 ([M]+).

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-4-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; Dow AgroSciences LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; WHITEKER, Gregory T.; US2014/275560; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 13194-68-8, name is 4-Iodo-2-methylaniline, 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 13194-68-8, Formula: C7H8IN

Compound 4 (5.67 g, 21.5 mmol) and dibutylhydroxytoluene (10 mg, 45 mumol) were dissolved in a mixed solution of toluene (10 ml) and dimethyl acetamide (10 ml). Thionyl chloride (1.50 ml, 20.7 mmol) was added dropwise to the resulting solution under ice cooling, and the solution was stirred at room temperature for 4 hours. Furthermore, a dimethyl acetamide solution (10 ml) of 4-iodo-2-methylaniline (2.00 g, 8.58 mmol) was added dropwise to the resulting solution under ice cooling, and the solution was stirred at 80 C. for 2 hours. After cooling the solution to room temperature, 1 N hydrochloric acid was added to the solution, followed by extraction with ethyl acetate. The organic layer obtained by the extraction was washed once with aqueous sodium bicarbonate and once with saline, respectively, and sodium sulfate was added to the washed organic layer. The obtained organic layer was filtered to collect the filtrate, and then the solvent was distilled off from the filtrate under reduced pressure. The resulting residue was purified by flash column chromatography to obtain Compound 8 (3.17 g) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodo-2-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; FUJIFILM Corporation; FUKUSHIMA, Yuki; GOTO, Ryoji; US2019/177268; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 111771-08-5, The chemical industry reduces the impact on the environment during synthesis 111771-08-5, name is 2-Fluoro-6-iodobenzoic acid, I believe this compound will play a more active role in future production and life.

Step A: 2-Fluoro-6-iodo-benzoic acid methyl ester. To a 200 mL round- bottomed flask were added 2-fluoro-6-iodo-benzoic acid (7.5 g, 28.2 mmol), LiOH*H2O (1 .42 g, 33.8 mmol), and THF (100 mL). The resulting mixture was warmed to 50 C and stirred for 2 h. Dimethyl sulfate (4.03 mL, 42.3 mmol) was then added and the mixture was warmed to 65 C. After 2 h, the mixture was cooled to room temperature and NH4CI(aq) (50 mL, 13 wt% solution) was added. The two resulting layers were thoroughly mixed and then separated. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a light brown oil (7.79 g, 99% yield). 1H NMR (400 MHz, CDCIs): 7.68 – 7.60 (m, 1 H), 7.15 – 7.06 (m, 2H), 3.98 (s, 3H).

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, 2-Fluoro-6-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50202; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 2974-94-9, name is 1-Iodo-4-phenoxybenzene, 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. HPLC of Formula: C12H9IO

Example 9 1-(2-{[3-(4-Phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine Using the general method of Example 7, 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.50 g, 1.88 mmol) was reacted with 4-iodophenyl phenyl ether (0.78 g, 2.63 mmol). The crude product was purified by column chromatography eluding with 95/5 dichloromethane/methanol to provide a solid. The solid was slurried with aqueous sodium hydroxide to remove salts and then purified by column chromatography eluding with 9/1 ethyl acetate/methanol to provide a solid. This material was further purified by column chromatography eluding with 99/1 ethyl acetate/methanol to provide 24 mg of 1-(2-{[3-(4-phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid, m.p. 146-148 C. Analysis. Calculated for C27H22N4O2.(H2O)4/5: %C, 72.24; %H, 5.30; %N, 12.48. Found: %C, 71.82; %H, 4.85; %N, 12.35. 1H NMR (300 MHz, DMSO-d6) delta 8.18 (s, 1H), 8.12 (d, J=7.4 Hz, 1H), 7.62 (d, J=7.7 Hz, 1H), 7.41-7.47 (m, 3H), 7.18-7.27 (m, 4H), 7.06 (dd, J=7.6, 1.0 Hz, 2H), 6.90 (dd, J=6.7 Hz, 2H), 6.71 (s, 2H), 4.85 (t, J=5.1 Hz, 2H), 4.37 (s, 2H), 4.02 (t, J5.0 Hz, 2H); IR (KBr) 3444, 3070, 2928, 1500, 1230, cm-1; HRMS (EI) Calculated for C27H22N4O2 (M+) 434.1743, found 434.1748.

The synthetic route of 1-Iodo-4-phenoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3M Innovative Properties Company; US6677348; (2004); B2;,
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. 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, A new synthetic method of this compound is introduced below., Safety of 2-Iodo-5-methylbenzoic acid

In a reactor, compound 15 (2.5 Kg, 9.54 mol) was dissolved in anhydrous methanol (10 L), and the concentrated sulfuric acid (360 mL, 7.16 mol) was slowly dripped into the reactor at room temperature. The reactor was heated to 65-80 C., and reacted for 18 hours. HPLC monitored that 5-7% of raw materials still remained. The reaction was supplemented with concentrated sulfuric acid (36 mL, 67.3 g) and continued to react for 18 hours. HPLC detected that the raw materials reacted completely.The reaction solution was cooled to 26 C. (four-pot reactions merged for treatment), and 10N sodium hydroxide solution (3.75 L) was slowly added to adjust pH to 5-6. The reaction solution was concentrated to about 35 L, and ethyl acetate (20 L), water (8 L), and 7% of sodium bicarbonate (10 L) were added into the reaction solution. Stirred and separated, the aqueous phase was extracted again with ethyl acetate (20 L), the organic phase was combined and washed with saturated brine (15 L), and dried over anhydrous sodium sulfate. The product solution was concentrated (-0.09 MPa, <55 C.) to obtain 2.5 Kg of product (yield: 95%) which was directly used for the next step without purification.1HNMR (DMSO-d6, 400 MHz) delta7.76 (d, J=8.4 Hz, 1H), 7.45 (s, 1H), 6.98 (d, J=8.0, 2.5H), 3.77 (s, 3H), 2.19 (s, 3H). 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; Shanghai Haiyan Pharmaceutical Technology Co., Ltd.; Yangtze River Pharmaceutical Group Co., Ltd.; Wu, Songliang; Luo, Zhi; Chen, Yuan; Wang, Yuhe; Qin, Dakun; Li, Xiaolin; Wang, Zheng; Li, Weidong; He, Haiying; (19 pag.)US10668066; (2020); B2;,
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. 58755-70-7, name is 1-Iodo-4-methoxy-2-nitrobenzene, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

To a solution of 4-iodo-3-nitroanisole (2.38 g, 8.50 mmol) in anhydrous THF (10 mL) at minus 40C under a nitrogen atmosphere, phenylmagnesium chloride (2 M in THF, 4.7 mL, 9.4 mmol) was added dropwise at a rate such that the temperature would not exceed minus 35C. Upon completion of the addition, the mixture was stirred at minus 40C for one hour, followed by addition of trimethylacetaldehyde (1.13 mL, 10.2 mmol). The mixture was stirred at minus 40C for two hours and then at room temperature for another one hour. The reaction was quenched with brine (100 mL), and the mixture was extracted with CH2CI2 (40 mL) three times. The combined organic phase was dried over a2S04 and concentrated in vacuo, and the residue was purified by silica gel column chromatography to yield racemic (R/5)-l-(4-methoxy-2-nitrophenyl)-2,2-dimethyl-l -propanol (1.52 g, 74%). 1H NMR (400 MHz, CDCl3): delta 7.67 (d, 1 H, J = 9.2 Hz, Ph-H), 7.22 (d, 1 H, J = 2.4 Hz, Ph-H), 7.12 (dd, 1 H, J= 8.8 and 2.8 Hz, Ph-H), 5.27 (d, 1 H, J= 4.0 Hz, Ph-CH), 3.86 (s, 3 H, OCH3), 2.01 (d, 1 H, J= 4.0 Hz, OH), 0.86 (s, 9 H, C(CH3)3).

The synthetic route of 58755-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LASERGEN, INC.; STUPI, Brian, Philip; LI, Hong; WU, Weidong; HERSH, Megan, N.; HERTZOG, David; MORRIS, Sidney, E.; METZKER, Michael, L.; WO2013/40257; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 5471-81-8, 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. 5471-81-8 name is Methyl 4-iodo-3-methylbenzoate, 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.

Under a protective atmosphere of inert gas, Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, were added to a 4.0 mL reaction flask equipped with a magnetic stir bar. 10mol%),Methyl 3-methyl-4-iodobenzoate (0.2 mmol, 1.0 equiv.),(R)-Benzyl glycidyl ether (0.6 mmol, 3.0 equiv.) and dry N-methylpyrrolidone (1.0 mL). The reaction flask was capped and stirred at room temperature for about 5 minutes, after which the mixture was heated to 80 C. Mix for 24 hours. The reaction vessel was cooled to rt then EtOAc (EtOAc)The Na2SO4 was dried, filtered and concentrated in vacuo. Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 10:1 (v/v),58 mg of methyl 7-methyl-2-(benzyloxymethyl)-2,3-dihydrobenzofuran-5-carboxylate (light yellow oily liquid, yield 93%, ee > 99%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-iodo-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
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. 3058-39-7, name is 4-Iodobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H4IN

The compound 4-cyanoiodobenzene 1a (0.023 g, 0.10 mmol, 1.0 eqv.) was added to the reactor in that order.DMSO (0.3 ml), Cs2CO3 (0.065 g, 0.20 mmol, 2.0 eq.).Phenol 2a (0.0113 g, 0.12 mmol, 1.2 eq.) was stirred at room temperature for 10 minutes.Then placed in an 80 C oil bath, reacted under light for 10 h,After the TLC detection reaction is completed, the reaction solution is subjected to filtration, extraction and column chromatography.The target product 3a was obtained in a yield of 83%.

The synthetic route of 3058-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Three Gorges University; Wang Long; Liu Na; Yang Qingqing; Hu Weimin; (6 pag.)CN109879779; (2019); A;,
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. 2996-31-8, name is 2-Fluoro-4-iodo-1-nitrobenzene, A new synthetic method of this compound is introduced below., Quality Control of 2-Fluoro-4-iodo-1-nitrobenzene

To a solution of compound 89-1 (450 mg, 1.69 mmol, 1.0 eq) in DMSO (5 mL) were added compound 89-la (116 mg, 1.69 mmol, 1.0 eq) and KF (98 mg, 1.7 mmol, 1.0 eq). The reaction mixture was stirred at 70 C for 2 hours. The mixture was diluted with water (30 mL) and the resultant mixture was extracted with EA (50 mL * 3). The combined organic layers were dried over Na2S04, filtered and concentrated to dryness under reduced pressure. The residue was purified by column chromatography over silica gel to afford the title compound 89-2 (200 mg, 37% yield). 1HNMR (400MHz, DMSO-c) delta 8.75 (s, 1H), 8.33 (s, 1H), 8.23 (d, J = 8.3 Hz, 1H), 8.01 (s, 1H), 7.97 (d, J= 8.3 Hz, 1H).

The synthetic route of 2996-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (294 pag.)WO2019/40380; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com