Author: Jessica.F

Some common heterocyclic compound, 56096-89-0, name is 4-Fluoro-2-iodobenzoic acid, molecular formula is C7H4FIO2, 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. Product Details of 56096-89-0

A mixture of 2-iodo-4-fluorobenzoic acid (194 mg, 0.73 mmol) and phosphorus pentachloride (152 mg, 0.73 mmol) in diethyl ether (5 mL) was stirred at room temperature for 2 h. The solvent was removed under reduced pressure to yield the 2-iodo-4-fluorobenzoyl chloride. [00465] A solution of 2-iodo-4-fluorobenzoyl chloride in tetrahydrofuran (5 mL) was added to a solution of 4-[3-aminobenzoyl]-1-methylpiperidine ketone (145 mg, 0.66 mmol) and triethylamine (0.5 mL, 3.6 mmol) in tetrahydrofuran (5 ml). The reaction mixture was stirred 16 h at room temperature. The reaction mixture was diluted with ethyl acetate and water then extracted with ethyl acetate. The ethyl acetate extracts were washed with 0.2N sodium hydroxide solution, water, brine, then dried over sodium sulfate. The solvent was removed under reduced pressure. Prepurified by eluting through a small amount of silica gel (5% 2M ammonia in methanol/methylene chloride) then purified by radial chromatography (silica gel, 2000 micron rotor, 2.5% 2M ammonia in methanol/methylene chloride) gave 266 mg of a white foam. Crystallized as the hydrochloric acid salt from ethyl acetate/ethanol then recrystallized from ethyl acetate/methanol to provide 120 mg (48%) of an off white powder. mp>250 C. MS(m/e) 467(M+1), 465(M-1). [00466] Analysis for C20H21ClFIN2O2: [00467] Calcd: C, 47.78; H, 4.21; N, 5.57; Found: C, 47.71; H, 4.14; N, 5.44.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 56096-89-0, its application will become more common.

Reference:
Patent; Eli Lilly and Company; US6777428; (2004); B1;,
Iodide – Wikipedia,
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Application 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.

In a microwave reaction vial with a magnetic stir bar, 4-chloro-3-iodoaniline (3) (1 eq, 0.4 mmol) was added, followed by 0.2 M HCl in D2O (1 eq, 2 mL). The vial was capped and sealed and heated in the microwave synthesis apparatus for 30 mins at a temperature of 180°C . The reaction mixture was cooled down and was quenched by additon of 2 mL 3 M NaOH, 1 mL brine and 2 mL Et2O, separating the organic phase and washing with brine.

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:
Article; Wang, Fangying; Jiang, Hongxia; Deng, Yufang; Yu, Jiang; Zhan, Miao; Zhao, Lifeng; Chen, Yuanwei; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2399 – 2402;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 51839-15-7,Some common heterocyclic compound, 51839-15-7, name is Dimethyl 5-iodoisophthalate, molecular formula is C10H9IO4, 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 mixture of dimethyl 5-iodo-benzerte-1,3-dicarboxylate (9) (320 mg, 1.00 mmol), bis(pinacolato)diborane (10) (279 mg, 1.10 mmol), potassium acetate (294 mg, 3.00 mmol), PdCl2(dppf)* (24 mg, 0.03 mmol) and dried DMF (6 mL) was stirred at 80C for 2 h. The reaction mixture was cooled to the room temperature. Then, dimethyl 5-iodo-benzene-1,3-dicarboxylate (9) (640 mg, 2.00 mmol), PdCl2(dppf) (24 mg, 0.03) and CsF (456 mg, 3.0 mmol; dissolved in 2.5 mL of water) were added. The mixture was stirred at 80C overnight and afterwards extracted for four times with diethylether (4 x 25 mL). The organic layer was dried with MgSO4 and the solvent was removed in vacuum. The crude product was purified by column chromatography (silica gel, ethylacetate/hexane, 3:7 v/v). Yield 82 %. M.p. 214-215 C. 1H-NMR (400 MHz, CDCl3): delta= 4.00 (s, 12H), 8.51 (d, 4H, J = 1.5 Hz), 8.72 (d, 2H, J = 1.5 Hz). 13C-NMR (100 MHz, CDCl3): delta= 52.5, 130.2, 131.5, 132.3, 139.9, 165.9. Rf= 0.50 (silica gel, othylacetate/hexane, 3:7 v/v). MS-EI, m/z (%): 386 (75) [M+], 355 (100), 327 (15), 194 (10). *[1,1′-bis(diphenylphoshino)ferrocene]dichloropalladium(II)].

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

Reference:
Patent; Technische Universitaet Carolo-Wilhelmina zu Braunschweig; EP1972338; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 5458-84-4, A common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, molecular formula is C7H6INO3, 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.

1-lodo-2-methoxy-4-nitro-benzene (6.01 g, 21.54 mmol) in absolute ethanol (127 mL) was cooled with an ice bath and treated with SnC (18.83 g, 99.31 mmol). The bath was removed and the mixture was stirred at room temperature for 4 h then poured into ice (300 mL), stirred and treated carefully with saturated aqueous sodium bicarbonate (250 mL) (pH 7-8). The solid was filtered with suction and the panel washed thoroughly with EtOAc (500 mL and 4 x 200 mL). The aqueous layer was separated, dried over sodium sulphate and evaporated. Purification of the crude by flash chromatography on silica gel (hexane/EtOAc 1/1) furnished the title compound (3.17 g, 59%).

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; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria, Gabriella; BERTRAND, Jay, Aaron; GNOCCHI, Paola; MOTTO, Ilaria; NESI, Marcella; PANZERI, Achille; VIANELLO, Paola; WO2013/14039; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

1450754-38-7, name is 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine, 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-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine

The steviol (30mg, 0.1mmol), K2CO3 (27mg, 0.2mmo 1) added to the dry flask, replace the nitrogen, then added 2mL anhydrous N, N-dimethylformamide (DMF), 3-(but-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine (1-1) (33mg0.13mmol) dissolved in 1mL N, N-dimethyl formamide, then added to the reaction under ice bath, and the mixture was heated to 70 C, and reacted for 6 hr. The mixture was subjected to thin layer chromatography (TLC), washed with 10% HCl, after washing with saturated brine and it was dried over anhydrous sodium sulfate and separation by column chromatography gave molecular probe 1 (white solid, 34 mg, 92% yield).

The synthetic route of 1450754-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Life Sciences Institute; Xiao Youli; Li Weichao; Zhou Yiqing; (27 pag.)CN108341781; (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. 624-76-0, name is 2-Iodoethanol, A new synthetic method of this compound is introduced below., Product Details of 624-76-0

0.874 g (11.5 mmol) of thioacetic acid was placed in a 100 mL three-necked flask under N2 protection,(10.0 mmol) of 2-iodoethanol and 1.749 g (11.5 mmol) of DBU were slowly added dropwise to the reaction solution. After completion of the dropwise addition, the mixture was left to stand at room temperature After the reaction, the reaction product was passed through a silica gel column (the particle size of the silica gel was 200 to 300 mesh), and the filtrate was collected to give 0.5 g of a yellow oily liquid, i.e., a middle The yield was 42%.

The synthetic route of 624-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liaoning University; Xia, Lin; Zhang, Aixia; Song, Peng; (14 pag.)CN104893710; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 610-97-9,Some common heterocyclic compound, 610-97-9, name is Methyl 2-iodobenzoate, molecular formula is C8H7IO2, 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 stirred slurry of methyl 2-iodo-benzoate (5.0 g, 0.019 mol) and N-bromosuccinimide (3.74 g, 0.021 mol) in acetic acid (10 mL) was added concentrated H2SO4 (10 mL) dropwise, keeping the temperature at 20-40 C. The mixture was stirred at room temperature for 88 hours and then heated at 50 C. for 4 hours. The mixture was cooled to 10 C., treated with 40 g of ice water, and extracted with 50 mL of CH2Cl2. The organic phase was washed in succession with 2×50 mL 5% NaHCO3, 50 mL 10% Na2S2O3, 50 mL water, and concentrated to colorless oil. The residue was purified by column chromatography (silica gel, 10:90 EtOAc:hexane) to provide the title compound. 1H NMR (CDCl3, 400 MHz) delta 7.92 (d, J=4 Hz, 1H), 7.83 (d, J=8 Hz, 1H), 7.27 (dd, J=8, 4 Hz, 1H), 3.92 (s, 3H); MS (DCl/NH3) [M+NH4]+ at 358, [M+NH3.NH4]+ at 375.

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

Reference:
Patent; Altenbach, Robert J.; Black, Lawrence A.; Chang, Sou-jen; Cowart, Marlon D.; Faghih, Ramin; Gfesser, Gregory A.; Ku, Yi-yin; Liu, Huaqing; Lukin, Kirill A.; Nersesian, Diana L.; Pu, Yu-ming; Curtis, Michael P.; US2005/256309; (2005); 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 35453-19-1 as follows. HPLC of Formula: C8H4I3NO4

5-Amino-2,4,6-triiodo-isophtalic acid (30 g, 0.054 mol), thionyl chloride (8.2 ml, 0.113 mol) and pyridine (0.2 ml) in 1 ,2 dichloroethane (20 ml) were heated to 70 0C. A portion of thionyl chloride (15.2 ml, 0.21 mol) was added dropwise during VA to 2 hrs, and the mixture was heated to 85 0C for 6 hrs. After cooling the reaction mixture to room temperature, it was poured into 30Og of ice-water. The yellow precipitate that formed was filtered off, sucked dry and then washed with water until washings showed a pH of ca 5. The filter cake was then dried in a vacuum oven at 500C for 3 hrs. A light yellow powder was obtained 31 g (~ quant.) as the desired product. 13C NMR (DMSOcZ6) 66, 78.4, 148.9, 149.2, 169 MS (ES-) found 593.5 [M-H+], expected 593.7

According to the analysis of related databases, 35453-19-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GE HEALTHCARE AS; WO2007/133090; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 52548-14-8,Some common heterocyclic compound, 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, molecular formula is C8H7IO2, 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.

Add 1.1 kg of acetone to the 5L reaction flask.131g 2-iodo-5-methylbenzoic acid,Stir and dissolve,Add 350g of anhydrous potassium carbonate,After heating to reflux (55-60 C) for half an hour, add 114g 1,2,3-triazole,2.4 g of cuprous iodide.The reaction was kept under reflux (55-60 C) for 8 hours, sampled, and sampled once every 1 h. After the reaction was completed, it was cooled to room temperature for filtration, and the filter cake was washed twice with 120 g of acetone to obtain a white solid at room temperature (20-30 C). The white solid was dissolved in 1.3 kg of purified water and stirred.After 30 min, hydrochloric acid was added dropwise at room temperature to adjust the pH of the system to 1.5-2.0 to obtain a large amount of white solid. It was stirred for 1-2 hours, filtered, and the filter cake was washed twice with purified water. The resulting solid was dried to dryness at 50 ± 5 C to give a crude compound.Add 1 compound of crude product, 0.2 kg of absolute ethanol and 0 kg of purified water to a 1 L reaction flask, and warm to 75-80 C.Clear, heat for half an hour, cool to 0-5 C, filter, filter cake with a cold ethanol solution rinse, to obtain a white solid compound 1 boutique.The compound 1 was placed in a blast drying oven at a temperature of 55 C ± 5 C and dried for 5 h. Sampling, sampling every 2h 1Time, until the test (rapid moisture analyzer: 105 C, 10 min) loss on drying ? 0.5%, get Suwoleisheng intermediate products -Compound 1 was fine white crystalline solid 86 g, yield: 93%. Purity: 99.91%, Cu < 5 ppm. The synthetic route of 52548-14-8 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Yangzijiang Pharmaceutical Group Co., Ltd.; Zou Yiquan; Xu Jingren; Cai Wei; Xuan Jingan; Chen Lingwu; Ji Ye; Zhu Yunlong; Liu Jinfeng; Hu Tao; (8 pag.)CN109810067; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 627-31-6, The chemical industry reduces the impact on the environment during synthesis 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), I believe this compound will play a more active role in future production and life.

Diiodopropane (0.295 g, 1.00 mmol, 5.0 eq) and potassium carbonate (0.028 g, 0.20 mmol, 1.0 eq) were added to a solution of the phenol 12 (0.100 g, 0.020 mmol, 1 .0 eq) in dry acetone (5 mL). The reaction mixture was heated at 60C for 6 hours when LC/MS showed complete reaction. The reaction mixture was concentrated to dryness under reduced pressure and the residue was purified by flash chromtography (silica gel, 75/25 v/v n- hexane/EtOAc to 50/50 v/v n-hexane/EtOAc) to afford the product as a colourless oil (0.074 g, 56%). LC/MS (3.853 min (ES+)), m/z: 669.0 [M+H]+. 1H NMR (400 MHz, CDCI3) delta 7.26 (s, 1 H), 6.90 (s, 1 H), 6.68 (s, 1 H), 6.24 (d, 1 H, J = 15.3 Hz), 5.87 (d, 1 H, J = 8.9 Hz), 5.78 (m, 1 H), 5.53 (m, 1 H), 5.12 (m, 2H), 4.65 (m, 2H), 4.41 (m, 1 H), 4.1 1 (m, 1 H), 3.93 (s, 3H), 3.81 (m, 1 H), 3.40 (t, 2H, J = 6.7 Hz), 3.05 (dd, 1 H, J = 16.3, 10.1 Hz), 2.57 (m, 1 H), 2.34 (m, 2H), 1 .84 (d, 3H, J = 6.6 Hz), 0.92 (s, 9H), 0.28 (s, 3H), 0.26 (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, 1,3-Diiodopropane(stabilized with Copper chip), other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SPIROGEN SARL; HOWARD, Philip Wilson; TIBERGHIEN, Arnaud; WO2013/53872; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com