Tag: M.W=200-300

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. 1031929-20-0, name is 4-Fluoro-2-iodobenzonitrile, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

ntermediate 87: 4-Fluoro-2-(pyrimidin-2-yl)benzoic acid.Step A: 2-lodo-4-fluorobenzonitrile (2.54 g, 10.3 mmol) and 2- tributylstannane pyrimidine (3.69 g, 10.0 mmol) were dissolved indomethoxyethane (18 mL) and treated with tetrakistriphenylphosphine palladium (0) (578 mg, 0.5 mmol) and copper (I) iodide (95 mg, 0.5 mmol). The reaction was then heated to 160 C for 90 minutes in the microwave. The reaction was cooled, concentrated under reduced pressure. Chromatography (20-100% EA in hexanes) gave the desired product. 1 H NMR (400 MHz, CDCIs): 8.93 (d, J = 4.9 Hz, 2H), 8.14 (dd, J = 9.6, 2.7 Hz, 1 H), 7.86 (dd, J = 8.6, 5.3 Hz, 1 H), 7.36 (t, J = 4.9 Hz, 1 H), 7.32 – 7.23 (m, 1 H).

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; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
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133232-56-1, name is 3-Iodo-2-methylbenzoic 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. Recommanded Product: 3-Iodo-2-methylbenzoic acid

(W02006117669 (Al)): To a solution of 3-iodo-2-methylbenzoic acid (5.00 g, l9.08mmol) in MeOH (20 mL) was added dropwise a solution of SOCh (4.16 mL, 57.24 mmol) in MeOH (10 mL) at 0 C. The mixture was heated to reflux for 3 h. The mixture was concentrated and the residue obtained was purified using S1O2 chromatography eluting with EtOAc in hexanes (0-15% EtOAc, gradient elution) to provide the title compound 5 as a brown oil (4.00 g, 75%). 1H NMR (500 MHz, CDC13) d 8.00 (dd, J = 1.3, 7.9 Hz, 1H), 7.76 (dd, J = 1.3, 7.7 Hz, 1H), 6.95 (td, J = 0.7, 7.8 Hz, 1H), 3.93 (s, 3H), 2.69 (s, 3H). HPLC-MS (ESI+): m/z 276.9 [100%, (M+H)+], 761.3 [72%, (M+Na)+]

The synthetic route of 133232-56-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; BURNETTE, Pearlie; LAWRENCE, Nicholas J.; LAWRENCE, Harshani; (0 pag.)WO2020/14489; (2020); A2;,
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Electric Literature of 51738-07-9, The chemical industry reduces the impact on the environment during synthesis 51738-07-9, name is 2-Chloro-6-iodobenzaldehyde, I believe this compound will play a more active role in future production and life.

The mixture of TsNHNH2 (3.16 mmol, 1.0 eq) and DME (6.0 mL) was stirred and heated to 60 Cuntil a clear solution was obtained. The mixture was cooled to 25 C, and then 2-chloro-6-iodobenzaldehyde (3.2 mmol, 1 eq) dissolved in DME (2 mL) was added dropwise to the mixtureunder stirring. After approximately 1 h, CuI (0.32 mmol, 10 mol %), diethyl H-phosphonate (2.88mmol, 1.0 eq) and Cs2CO3 (4.74 mmol, 1.5 eq) were added sequentially to the reaction mixture at25 C. The mixture was then heated under stirring at 80 C for 3 h. When the reaction wascomplete (TLC control), the mixture was allowed to cool to 25 C. It was then filtered through ashort plug of SiO2 (AcOEt). The solvent was evaporated in vacuum. The residue was purified bysilica gel column chromatography (40 % EtOAc/petroleum ether) to afford an oil, 0.40 g, (35%).

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-Chloro-6-iodobenzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Roehrig, Ute F.; Majjigapu, Somi Reddy; Caldelari, Daniela; Dilek, Nahzli; Reichenbach, Patrick; Ascencao, Kelly; Irving, Melita; Coukos, George; Vogel, Pierre; Zoete, Vincent; Michielin, Olivier; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4330 – 4333;,
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Adding a certain compound to certain chemical reactions, such as: 870606-29-4, name is 5-Chloro-3-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 870606-29-4, Application In Synthesis of 5-Chloro-3-iodo-2-methylaniline

To a solution of 5-chloro-3-iodo-2-methylaniline (1.32 g, 4.9 mmol) in diglyme (5 mL) was added potassium carbonate (677 mg, 4.9 mmol) and bis(2-chloroethyl)amine hydrochloride (875 mg, 4.9 mmol). The mixture was refluxed for 24 h and then cooled to room temperature. Water and ethyl acetate were added. The layers were separated, the organic layer was dried over sodium sulfate, filtered, and concentrated. Column chromatography on silica (dichloromethane:methanol 4:1) provided 1-(5-chloro-3-iodo-2- methylphenyl) piperazine as a white solid (660 mg, 40% yield). IH NMR (400 MHz, CDC13) 8 7.56 (d, 1H), 6.97 (d, 1H), 3.03 (m, 4H), 2.83 (m, 4H), 2.39 (s, 3H), 1.73 (br s, 1H); MS (ESI) for C11H14ClIN2: 337 (MH+).

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-Chloro-3-iodo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EXELIXIS, INC.; WO2005/117909; (2005); A2;,
Iodide – Wikipedia,
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Electric Literature of 351447-07-9, These common heterocyclic compound, 351447-07-9, name is 6-Iodo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine, 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 5-(3,4-Dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)-pent-4-ynoic acid butyl ester (4-5) A suspension of 4-4 (0.113 g, 0.431 mmol) and n-butyl 4-pentynoate (0.0731 g, 0.474 mmol) in triethylamine (3.0 mL) was purged with Ar, then cooled to 0 C. Copper iodide (0.0021 g, 0.0108 mmol) and Pd(PPh3)2Cl2 (0.0076 g, 0.0108 mmol) were added, the ice bath was removed after ten minutes, and the resulting suspension was stirred overnight. The mixture was then partitioned between EtOAc and saturated NaHCO3 solution. The organic phase was washed with sat. NaHCO3 solution, water, and brine, then dried with MgSO4 and concentrated. Flash chromatography (silica, 45% EtOAc-Hexanes) yielded a clear, yellowish oil. 1H-NMR (CDCl3): delta 6.88 (d, J=7.9 Hz, 1 H), delta 6.69 (d, J=8.0 Hz, 1 H), delta 5.07 (br s, 1 H), delta 4.22 (t, J=4.4, 2 H), delta 4.10 (t, J=6.7 Hz, 2 H), delta 3.54 (m, 2 H), delta 2.70 (m, 2 H), delta 2.61 (m, 2 H), delta 1.61 (m, 2 H), delta 1.38 (m, 2 H), delta 0.92 (t, J=7.4 Hz, 3 H). MS (M++H) 289.1.

Statistics shows that 6-Iodo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine is playing an increasingly important role. we look forward to future research findings about 351447-07-9.

Reference:
Patent; Askew, Ben C.; Breslin, Michael J.; Duggan, Mark E.; Hutchinson, John H.; Meissner, Robert S.; Perkins, James J.; Steele, Thomas G.; Patane, Michael A.; US2001/53853; (2001); A1;,
Iodide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 42048-11-3, name is 2-Chloro-6-iodotoluene, 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 42048-11-3, name: 2-Chloro-6-iodotoluene

0.3 mmol of sodium carbonate, 0.1 mmol of diphenylacetylene, 0.005 mmol of palladium acetate, 0.005 mmol of bis(2-diphenylphosphinophenyl)ether, and 0.15 mmol of boronic acid pinacol ester.0.15mmol of 2-methyl-3-chloroiodobenzene and 1mL of N,N-dimethylformamide were added to a 15mL reaction tube, and the nitrogen was repeatedly filled 10 times, placed in an oil bath at 120 C for 24 hours; cooling The reaction solution was diluted with ethyl acetate and washed with water three times.The organic phase was dried over anhydrous Na2SO4, filtered and concentrated.Purification by thin layer chromatography gave 18.5 mg of the desired product in a yield of 43%. The nuclear magnetic and high resolution mass spectra of this compound are characterized as follows:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-6-iodotoluene, and friends who are interested can also refer to it.

Reference:
Patent; Huaqiao University; Cheng Guolin; Lv Weiwei; (10 pag.)CN109879899; (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. 42048-11-3, name is 2-Chloro-6-iodotoluene, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

A solution of a (1.8 g, 6 8 mmol, 1.0 eq), b (1 0 g, 7.5 mmol, 1 1 eq), KOAc (2 0 g, 20.4 mmol, 3.0 eq), copper powder (132.0 mg, 2 0 mmol, 0.3 eq), and CuiOAc)?. (364.0 mg, 2.0 mmol, 0.3 eq) in 2-pentanol (50.0 mL) was stirred at 140 C overnight under N?. atmosphere, then cooled to room temperature. The mixture was filtered and the filtrate was concentrated to give crude e (2 2 g, ca.100%) LC/MS: 262.0

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; SILICON SWAT, INC.; CHAMBERLAIN, Brian T.; RICE, James M.; JERNIGAN, Finith E., III; SHERMAN, Woody; KULKARNI, Meghana M.; SHECHTER, Sharon; ALLEN, Bryce K.; TAN, Dazhi; MARINO, Kristen A.; LIN, Zhixiong; (292 pag.)WO2019/100061; (2019); A1;,
Iodide – Wikipedia,
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Application of 52914-23-5, The chemical industry reduces the impact on the environment during synthesis 52914-23-5, name is 2-(4-Iodophenyl)ethanol, I believe this compound will play a more active role in future production and life.

(a) 104 g of p-iodophenethyl alcohol was combined in solution with 216 g of hydrobromic acid (48%) and 36 g of thiourea in 100 ml of water and reacted in accordance with the procedure outlined in Example I(a). Vacuum distillation at 91-95 and 0.2 mm Hg gave a 27% yield of p-iodophenethyl thiol having a refractive index of n25 D = 1.6411, an ALD of 0.56 ml/Kg and a formula of C8 H8 IS.

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-(4-Iodophenyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Alcon Laboratories, Inc.; US4125554; (1978); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 7212-28-4,Some common heterocyclic compound, 7212-28-4, name is 2-Iodo-N-phenylacetamide, molecular formula is C8H8INO, 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: A mixture of DDPT (0.5 g), 6a-j (1.57 mmol) and K2CO3 (0.45 g, 3.26 mmol) in acetone (20 mL) was refluxed for 2 h. The reaction mixture was evaporated in vacuo, and purified by column chromatography (CH2Cl2: AcOEt = 32:1) to give compounds 7a-j. 1.6.1. 2-(4-Deoxyl-4′-demethylpodophyllotoxin-oxy)-N-phenylacetamide(7a)The title compound wasobtained in 44.6% yield as a white solid: mp 210-212 C; IR numax (cm-1) 3337,3040, 2962, 2909, 2878, 2842, 1767, 1690, 1597, 1537, 1504, 1483, 1462, 1443,1418, 1331, 1240, 1224, 1156, 1037, 932; 1H NMR (300 MHz, CDCl3)delta 9.58 (s, 1H, ArNH), 7.63 (d, J = 7.9Hz, 2H, ArH), 7.36 (t, J =7.8 Hz, 2H, ArH), 7.13 (t, J = 7.3Hz, 1H, ArH), 6.69 (s, 1H, ArH), 6.53 (s, 1H, ArH), 6.42 (s, 2H, ArH), 5.96 (d,J = 6.8 Hz, 2H, -OCH2O-), 4.64-4.62 (m, 3H, -OCH2CO-, CH), 4.59-4.35(m, 1H, -OCH2-), 4.11-3.74 (m, 1H, -OCH2-), 3.82 (s, 6H,2 ¡Á CH3), 3.12-3.07 (m, 1H, -CH2-), 2.84-2.76 (m, 3H,-CH-, -CH2-); ESI calcd. 516.2 [M – H]-, found 516.0 [M -H]-. HRMS calcd. C29H27NO8Na [M +Na]+ 540.1634, found 540.1646 (parts per million error of 2.2).

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

Reference:
Article; Zhu, Xiong; Fu, Junjie; Tang, Yan; Gao, Yuan; Zhang, Shijin; Guo, Qinglong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 4; (2016); p. 1360 – 1364;,
Iodide – Wikipedia,
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116632-14-5, name is 3-Iodonaphthalen-2-amine, 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. Application In Synthesis of 3-Iodonaphthalen-2-amine

Compound (3-1) (3-iodonaphtalen-2-amine, 1.00 g, 3.72 mmol), copper iodide (0.21 g, 1.11 mmol), potassium carbonate (1.02 g, 7.44 mmol), and dimethylsulfoxide (DMSO, 37 ml) are put in a reaction vessel, after argon gas is substituted for gas therein, and then, stirred. Subsequently, Compound (3-2) (benzoylthiocyanate, 1.81 g, 11.15 mmol) is added thereto, and the obtained mixture is stirred at 90 C. for 12 hours. The resultant is cooled down to room temperature, water is added thereto, the obtained mixture is cooled down to room temperature, and water is added thereto, an organic layer is extracted therefrom with ethyl acetate and dried with anhydrous sodium sulfate, and a solvent therein is distilled under a reduced pressure and removed. A residue therefrom is purified through silica gel column chromatography (hexane:ethyl acetate in a volume ratio of 5:1) to obtain Compound (3-3) (N-(naphtho[2,3-d]thiazol-2-yl)benzamide, 0.60 g). This solid is dissolved in methanol (35 ml). Then, 10 ml of a 2N sodium hydroxide aqueous solution is added thereto, and the obtained mixture is heated and stirred for one night. Subsequently, 100 ml of water is added thereto, and a solid precipitate therein is filtered and obtained. The solid is twice washed with water (30 ml) and dried to obtain Compound (3-4) (naphtho[2,3-d]thiazole-2-amine(naphtho[2,3-d]thiazol-2-amine, 0.26 g, a yield of 35%).

The synthetic route of 116632-14-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Electronics Co., Ltd.; Ishii, Norihito; Shibata, Katsunori; Ro, Takkyun; Kwon, Ohkyu; Kim, Sang Mo; Park, Kyung Bae; Yun, Sung Young; Leem, Dong-Seok; Lim, Youn Hee; Jin, Yong Wan; Choi, Yeong Suk; Choi, Jong Won; Choi, Taejin; Choi, Hyesung; Heo, Chul Joon; (50 pag.)US2019/51833; (2019); A1;,
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