Tag: M.W=200-300

Synthetic Route of 135050-44-1, A common heterocyclic compound, 135050-44-1, name is 3-Chloro-4-iodoaniline, molecular formula is C6H5ClIN, 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.

STEP D: 2-chloro-2′-methyl-4′-(trifluoromethyl)-[1,1′-biphenyl]-4-amine 3-Chloro-4-iodoaniline (3.0 g, 11.8 mmol), (2-methyl-4-(trifluoromethyl)phenyl)boronic acid (2.9 g, 14.2 mmol), Pd(dppf)Cl2 (1.0 g, 1.2 mmol), and K2CO3 (3.3 g, 23.7 mmol) were dissolved in 1,4-dioxane (40 mL) and water (10 mL) and the resulting mixture was heated to 80 C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

The synthetic route of 135050-44-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chakravarty, Devraj; Greco, Michael; Shook, Brian; Xu, Guozhang; Zhang, Rui; US2012/302641; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 460-37-7,Some common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, molecular formula is C3H4F3I, 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.

Methyl 1H-1,2,4-triazole-3-carboxylate (8.11 g, 63.8 mmol) was dissolved in DMF (41 ml) andcooled to 0C. Sodium hyride (3.32 g, 60% purity, 82.9 mmol) was added and the reaction mixturewas stirred for 30 mm at 0C. After 1,1,1-trifluoro-3-iodopropane (15.0 g, 67.0 mmol) was added the reaction mixture was stirred for 16 h at room temperature. Aqueous ammoniumchloride solution and ethyl acetate were added. Layers were separated and aqueous layer was extracted with ethyl acetate. Combined organic extracts were washed with brine, dried with sodium sulfate andsolvents were removed in vacuo. The crude product was purified by preparative HPLC (Method 4) affording 2.56 g (18% of th.) of the title compound?H-NMR (400 MHz, DMSO-d6) oe [ppm]: 2.904 (0.96), 2.921 (2.07), 2.932 (2.97), 2.938 (1.52),2.948 (5.97), 2.959 (3.22), 2.966 (3.45), 2.976 (5.83), 2.987 (1.41), 2.993 (3.06), 3.004 (1.93),3.021 (0.94), 3.331 (1.18), 4.556 (8.10), 4.573 (16.00), 4.590 (7.72), 8.776 (11.85).

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-Trifluoro-3-iodopropane, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; COLLIN-KROePELIN, Marie-Pierre; KOLKHOF, Peter; NEUBAUER, Thomas; FUeRSTNER, Chantal; POOK, Elisabeth; TINEL, Hanna; SCHMECK, Carsten; WASNAIRE, Pierre; SCHIRMER, Heiko; LUSTIG, Klemens; (131 pag.)WO2019/81306; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 103440-52-4, 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. 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 2-iodo-5-methylbenzoate in 2-MeTHF (25 mL) triethylamine (3.0 mL, 21.7 mol) was added and the solution was degassed with N2. Pinacol borane (1.56 mL, 10.8 mol) was added slowly (over 15 minutes) to the stirring solution while maintaining the purge. The solution was further degassed for 10 minutes and Tri-o- tolylphosphine (110 mg, 0.36 mol) was added followed by Palladium (II) acetate (50 mg, 0.22mol). This caused the reaction to turn black immediately with a slow exothermic from 1 1 C to 25 C. At this point a delayed exothermic was observed and the reaction temperature increased to 60 C (over 45 minutes). The reaction temperature was increased to 77 C and aged for 2 hours. The heat source was removed and the reaction was cooled for 1 hour. A 26 w/w% ammonium chloride solution was added very slowly to control gas evolution and exothermic which caused a black precipitated to form. The supernatant was transferred to the extractor which already contained 43 mL of water. The remaining black slurry was filtered and washed with diethyl ether. The solution was transferred to a separatory funnel and the layers were separated The crude was purified by FC on silica gel (eluent: Cy/EtoAc 8/2) affording methyl 5-methyl-2-(tetramethyl-1 ,3,2- dioxaborolan-2-yl)benzoate (p59, 1 .51 g, y=76%). MS (mlz): 276.0 [M]+.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-Iodo-5-methylbenzoate. I believe this compound will play a more active role in future production and life.

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

Reference of 573764-31-5,Some common heterocyclic compound, 573764-31-5, name is 4-Chloro-3-iodoaniline, molecular formula is C6H5ClIN, 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.

E: EDC Amide Bond Formation Carboxylic acid (1.1 eq) was added to a solution of aniline (1.0 eq) and EDC (1.4 eq) in methylene chloride (0.7 M in aniline). The solution was stirred at 23° C. for 2 hours, poured onto a 1:1 mixture of saturated aq. NH4Cl and water, extracted twice with methylene chloride, dried (MgSO4), and concentrated. Purification of the crude product by chromatography on silica gel (conditions given below) afforded the desired product.; Example 5 5-Acetyl-N-(4-chloro-3-(pyridin-2-yl)phenyl)thiophene-2-carboxamide 4-Chloro-3-iodoaniline (2.5 g, 9.88 mmol) was used in Procedure E with 5-acetylthiophene-2-carboxylic acid (1.85 g, 10.8 mmol) at 23° C. for 2 hours. The crude material was purified by silica gel chromatography (20-100percent ethyl acetate/hexanes) to yield 5-Acetyl-N-(4-chloro-3-iodophenyl)thiophene-2-carboxamide as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-iodoaniline, its application will become more common.

Reference:
Patent; Gunzner, Janet L.; Sutherlin, Daniel; Stanley, Mark S.; Bao, Liang; Castanedo, Georgette M.; Lalonde, Rebecca L.; Wang, Shumei; Reynolds, Mark E.; Savage, Scott J.; Malesky, Kimberly; Dina, Michael S.; US2006/63779; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 72373-82-1, 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. 72373-82-1, name is 1-Chloro-2-fluoro-3-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 17A. Ethyl l-(3-chloro-2-fluorophenyl)-lH-imidazole-4- carboxylate, 1 HQ: A mixture of l-chloro-2-fluoro-3-iodobenzene (0.549 g, 2.141 mmol), ethyl lH-imidazole-4-carboxylate (0.3 g, 2.141 mmol), copper(I) iodide (0.082 g, 0.428 mmol), L-proline (0.099 g, 0.856 mmol), and K2C03 (0.888 g, 6.42 mmol) in DMSO (4.28 mL) was vacuumed and back-filled with argon for three times, then capped and heated at 110 °C. After 20 h, the reaction mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with H20, brine, dried over Na2S04, filtered, and concentrated. The crude product was then purified using reverse phase HPLC chromatography to yield the desired product (0.01 g, 1.2percent) as a colorless oil. MS (ESI) m/z: 269.0 (M+H)+.Intermediate 17A. Ethyl l-(3-chloro-2-fluorophenyl)-lH-imidazole-4- carboxylate, 1 HQ: A mixture of l-chloro-2-fluoro-3-iodobenzene (0.549 g, 2.141 mmol), ethyl lH-imidazole-4-carboxylate (0.3 g, 2.141 mmol), copper(I) iodide (0.082 g, 0.428 mmol), L-proline (0.099 g, 0.856 mmol), and K2C03 (0.888 g, 6.42 mmol) in DMSO (4.28 mL) was vacuumed and back-filled with argon for three times, then capped and heated at 110 °C. After 20 h, the reaction mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with H20, brine, dried over Na2S04, filtered, and concentrated. The crude product was then purified using reverse phase HPLC chromatography to yield the desired product (0.01 g, 1.2percent) as a colorless oil. MS (ESI) m/z: 269.0 (M+H)+.

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, 1-Chloro-2-fluoro-3-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; SMITH, II, Leon M.; ORWAT, Michael J.; JEON, Yoon; CORTE, James R.; WO2014/160668; (2014); 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. 14452-30-3, name is 1-(3-Iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-(3-Iodophenyl)ethanone

1-[3-(2,6-difluorobenzyl)-phenyl]-ethanone (8A). A suspension of Dibromoethane (0.28 mL, 0.0032 mole) in 35 mL of THF under Argon was treated with activated zinc (10.5 g, 0.161 mole) and heated to reflux 2 times for 30 seconds each time. The suspension was then cooled in a salt water ice bath to -8 C. and 2,6-Difluorobenzyl bromide (16.8 g, 0.081 mole) in 20 mL of THF was added dropwise. After addition was completed the reaction was allowed to stir at 0 C., for 1 hour. In a separate flask was added Bis(dibenzylideneacetone)palladium (3.1 g, 0.00537 mole), Tri(2-furyl) phosphine (2.5 g, 0.0107 mole), and 3-iodoacetophenone (13 g, 0.0537 mole) to 40 mL of THF and cooled to 0 C. The zinc suspension was then cannulated into the 3-iodoacetophenone mixture and the ice bath was removed. After 18 hours the mixture was filtered through a pad of celite and washed several times with EtOAc and then the solvents were removed under reduced pressure. The residue was treated with 150 mL of a saturated aqueous solution of NH4Cl and extracted with EtOAc three times, the combined organic layers were dried over NaSO4, filtered and evaporated to give a brown oil. This crude product was flash chromatographed with 15% EtOAc/Hexanes to give 1-[3-(2,6-difluoro-benzyl)-phenyl]-ethanone (8A) as a yellow oil. Rf=0.56 (15% EtOAc/Hexanes). 1H NMR (400 MHz, CDCl3) delta 7.86 (s, 1H), 7.78 (d, j=7.6 Hz, 1H), 7.45 (d, j=8.3 Hz, 1H), 7.36 (t, j=7.6 Hz 1H), 7.19 (m, 1H), 6.89 (m, 2H), 4.07 (s, 2H), 2.57 (s, 3H)

According to the analysis of related databases, 14452-30-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Payne, Linda S.; Tran, Lekhanh O.; Zhuang, Linghang H.; Young, Steven D.; Egbertson, Melissa S.; Wai, John S.; Embrey, Mark W.; Fisher, Thorsten E.; Guare, James P.; Langford, H. Marie; Melamed, Jeffrey Y.; Clark, David L.; US2003/229079; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6293-83-0, name is 2-Iodo-4-nitroaniline, 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. Computed Properties of C6H5IN2O2

General procedure: A mixture of compound2 (1.0 equiv), 10% Pd/C (0.016 equiv), PPh3 (0.125 equiv), CuI (0.02 equiv), and triethylamine (2 equiv) in ethanol (5 mL) was stirred at 25-30 C for 30 min under nitrogen. To this was added iodoarene (3) (1.0 equiv), and the mixture was initially stirred at room temperature for 1 h and then at 70 C for the time indicated in Table 2. After completion of the reaction, the mixture was cooled to room temperature, diluted with EtOAc (50 mL), and filtered through Celite.The organic layers were collected, combined, washed with water (3 30 mL),dried over anhydrous Na2SO4, filtered, and concentrated under low vacuum.The crude residue was purified by column chromatography on silica gel using methanol/dichloromethane to afford the desired product.

The synthetic route of 6293-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Babu, P. Vijaya; Gorja, Dhilli Rao; Meda, Chandana Lakshmi T.; Deora, Girdhar Singh; Kolli, Sunder Kumar; Parsa, Kishore V.L.; Mukkanti; Pal, Manojit; Tetrahedron Letters; vol. 55; 20; (2014); p. 3176 – 3180;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 58313-23-8,Some common heterocyclic compound, 58313-23-8, name is Ethyl-3-iodobenzoate, molecular formula is C9H9IO2, 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.

Ethyl 3-iodobenzoate (939mg, 3.4Ommol) was dissolved in DIVIF (2mL) and a solution of 3-cyanophenylboronic acid (500mg, 3.4Ommol) in DIVIF (5mL) was added. A solutionof Pd(OAc)2 (15mg, 0.O68mmol) and Na2CO3 (858mg, 10.2mmol) in water (2mL) wasadded and the reaction mixture was heated at 110C for 2d. The reaction mixture was concentrated in vacuo and partitioned between DCM (1 5OmL) and water (5OmL). The aqueous fraction was extracted with DCM (5OmL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo. The residue was purified by columnchromatography to give the title compound (767mg, 90%) as a pale yellow liquid.LCMS: ES 252.1 [IVIHf.

The synthetic route of 58313-23-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROXIMAGEN LIMITED; MEO, Paul; STEWART, Alison; HOBBS, Christopher; WO2014/20351; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 153898-63-6, These common heterocyclic compound, 153898-63-6, name is 2-Iodo-5-methoxyaniline, 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.

Bis(triphenylphosphine)palladium(ll) dichloride (32,1 mg; 45,8 muiotatauiotaomicronIota), copper(l) iodide (17,8 mg; 91,5 muiotatauiotaomicronIota), 2-lodo-5-methoxyaniline (1,2 g; 4,6 mmol), phenylacetylene (573 ml; 5,5 mmol), and diethylamine (10 ml) are refluxed for 2 h. The residue is chromatographed on silica gel (heptane/EE, 10/1) to afford 5-methoxy-2-(phenylethynyl)aniline (818 mg; 3.7 mmol; 80% of theory). 1H NMR (500 MHz, Chloroform-d) delta 7.54 (d, J = 6.7 Hz, 2H), 7.36 (q, J 8.9, 7.7 Hz, 2H), 7.32 (q, J = 8.9, 8.5 Hz, 2H), 6.34 (dd, J = 8.5, 2.4 Hz, 1H), 6.30 (d, J = 2.3 Hz, 1H), 3.82 (s, 3H).

Statistics shows that 2-Iodo-5-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 153898-63-6.

Reference:
Patent; MERCK PATENT GMBH; DOBELMANN-MARA, Lars; RIEDMUELLER, Stefan; SCHRAUB, Martin; (166 pag.)WO2018/149853; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 1829-28-3 as follows. Recommanded Product: 1829-28-3

In a typical run, 4-isopropylphenylboronic acid (200 mg, 1.22 mmol) was taken up in 4 mL of DMF along with ethyl 2-iodobenzoate, [1,1 ‘-bis(diphenylphosphino)- ferrocene]dichloropalladium (II) complex with CH2Cl2 (149 mg, 15 molpercent) and anhydrous Na2CO3 (194 mg, 1.83 mmol). The reaction mixture was heated in a microwave reactor at 140 0C for 45 min. It was then cooled to room temperature and diluted with EtOAc. The organic layer was washed with water, dried (Na2SO4) and concentrated under reduced pressure to afford crude ethyl 4’-isopropylbiphenyl-2-carboxylate.

According to the analysis of related databases, 1829-28-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2008/100423; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com