Tag: M.W=200-300

Electric Literature of 202982-67-0, 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. 202982-67-0, name is 4-Chloro-3-fluoroiodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a) (4-Chloro-3-fluoro-phenyl)-propynoic acid ethyl ester (Vd) Under argon atmosphere, a four neck flask was charged with 1-chloro-2-fluoro-4-iodo-benzene (50.5 g, 0.20 mol), bis(triphenylphosphine) palladium(II) chloride (2.76 g, 3.94 mmol, 2 mol %), copper(I) iodide (1.50 g, 7.80 mol, 4 mol %) and dry THF (600 ml). At r.t., cesium carbonate (128.3 g, 0.39 mol, 2 eq.) was added over 5 min. Finally, propynoic acid ethyl ester (38.6 g, 0.39 mol, 2 eq.) was added, and the reaction was stirred for 48 h at 35 C. The reaction mixture was evaporated to dryness, and the residue was taken up in toluene (50 ml) and heptane (100 ml). The resulting suspension was stirred at 40 C. for 1 h and filtered afterward over celite. The filtrate was concentrated, and the product was purified by silica gel filtration (toluene/heptane 1:2) to yield 38.8 g (87%) of the Vd as a light yellow solid. ES-MS m/e: 227.2 (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, 4-Chloro-3-fluoroiodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-Emery, Fabienne; Puentener, Kurt; Ratni, Hasane; US2010/152462; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 60577-34-6,Some common heterocyclic compound, 60577-34-6, name is 4-Iodo-N-methylaniline, molecular formula is C7H8IN, 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.

7.1. Methyl 6-cyano-1-methyl-2-oxo-1,2-dihydro-4-quinolineacetate 1.1 ml of trimethylsilyl cyanide (8.4 mmol) followed by 0.15 g (0.13 mmol) of tetrakistriphenylphosphinepalladium are added to a solution of 0.50 g (1.4 mmol) of methyl 6-iodo-1-methyl-2-oxo-1,2-dihydro-4-quinolineacetate (prepared from N-methyl-4-iodoaniline according to the method described in Example 1) in 6 ml of anhydrous triethylamine. The reaction medium is then heated to reflux for 4 hours under a nitrogen atmosphere. After cooling to room temperature, the medium is poured into 60 ml of toluene and 60 ml of water. The organic phase is washed with water and the initial aqueous phase is re-extracted with dichloromethane. The organic phases are combined, dried over sodium sulphate and concentrated under vacuum. The residue is purified by flash chromatography on silica, eluding with a methanol/dichloromethane (5:95) mixture. 0.313 g of the expected nitrile is obtained. Yield=87%; Melting point=202-203 C.

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

Reference:
Patent; SYNTHELABO; US5958924; (1999); A;,
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.

1, 2, 3-Triazole (3.45 g, 50 mmol) , 2-iodo-5-methylbenzoic acid (5.24 g, 20 mmol) , cesium carbonate (11.72 g, 36 mmol) , trans-N, N’-dimethyl-1, 2-cyclohexanediamine (0.51 g, 3.60 mmol) , cuprous iodide (0.38 g, 2 mmol) and N, N-dimethylformamide (30 mL) were added sequentially to a 100 mL of single-necked round-bottomed flask under nitrogen, and the mixture was warmed gradually to 100 and reacted for 4 h. The reaction mixture was cooled, diluted with water, and extracted with ethyl acetate (200 mL x 2) . The aqueous layer was acidified to pH 12 with concentrated hydrochloric acid, and the resulting mixture was extracted with ethyl acetate (200 mL x 2) . The combined organic layers were dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel eluted with (dichloromethane/methanol (v/v) 50/1) to give the title compound (as a yellow solid, 2.76 g, 68) .[MS (ESI, neg. ion) m/z: 202.1 [M-H]- and1H NMR (CD3OD, 600 MHz) delta (ppm) : 7.88 (s, 2H) , 7.66 (d, 1H) , 7.59 (d, J 8.2 Hz, 1H) , 7.507.48 (dd, J 8.1 Hz, 1.1 Hz, 1H) , 2.45 (s, 3H) .13C NMR (CD3OD, 151 MHz) delta (ppm) : 169.8, 140.7, 137.5, 136.7, 133.5, 131.5, 129.3, 126.0, 21.0.

The synthetic route of 52548-14-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; GAO, Jinheng; ZHANG, Ji; (107 pag.)WO2017/12502; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103440-52-4, A common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, molecular formula is C9H9IO2, 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 methyl 2-iodobenzoate (5a) (262 mg, 1.00 mmol) and benzophenone (2a)(275 mg, 1.51 mmol, 1.51 equiv) dissolved in THF (5.0 mL) was slowly added(trimethylsilyl)methylmagnesium chloride (0.983 M, THF solution, 3.05 mL, 3.00 mmol,3.00 equiv) at room temperature. After stirring for 12 h at the same temperature, to themixture was added an aqueous saturated solution of ammonium chloride (10 mL). Themixture was extracted with EtOAc (10 mL ¡Á 3), and the combined organic extract waswashed with brine (5 mL), dried (Na2SO4), and after filtration, the filtrate was concentratedunder reduced pressure. The residue was purified by flash column chromatography (silica-gel16 g, n-hexane/EtOAc = 10/1) to give 3,3-diphenyl-3H-isobenzofuran-1-one (6a) (250 mg,0.873 mmol, 87.3%) as a colorless solid.

The synthetic route of 103440-52-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nakamura, Yu; Yoshida, Suguru; Hosoya, Takamitsu; Chemistry Letters; vol. 46; 6; (2017); p. 858 – 861;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

61272-76-2, name is 4-Fluoro-2-iodoaniline, 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. Safety of 4-Fluoro-2-iodoaniline

Example 26 1-Benzyl-4-(((2-(tert-butyldimethylsilyl)-5-fluoro-1H-indol-3-yl)methoxy)methyl)-N,N-dimethylcyclohexanamine (non-polar diastereomer) In a heated flask with a Schlenk attachment a mixture of Ain-04 (400 mg, 1 mmol), 4-fluoro-2-iodoaniline (Ian-04, 284 mg, 1.2 mmol), sodium carbonate (530 mg, 5 mmol) and [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II) dichloride (PEPPSI, 136 mg, 0.2 mmol) was evacuated, flushed with argon and then N,N-dimethyl formamide (6 ml) was added. The reaction mixture was stirred for 20 h at 100¡ã C. and then concentrated to small volume under vacuum. Toluene was added three times to the residue, which was concentrated to dryness again each time, and then diethyl ether (30 ml) was added. The mixture was washed with water (10 ml) and the precipitated deposit was filtered off. The organic phase was washed with 1 M sodium thiosulfate solution (10 ml), sodium chloride solution (10 ml) and with water (10 ml), dried with sodium sulfate and concentrated to small volume under vacuum. The crude product (590 mg) was purified by flash chromatography (40 g, 23*2.5 cm) with methanol, purified again by flash chromatography (18 g, 18*2 cm) with chloroform/methanol (95:5) and by a further flash chromatography (20 g, 13*2.5 cm) with ethyl acetate/cyclohexane (1:2). Yield: 289 mg (57percent), yellowish solid Melting point: 58-62¡ã C. 1H-NMR (DMSO-d6): 0.35 (s, 6H); 0.85 (s, 9H); 0.87-1.00 (m, 2H); 1.13-1.35 (m, 5H); 1.77 (d, J=13.1 Hz, 2H); 2.20 (s, 6H); 2.55 (s, 2H); 3.19 (d, J=5.4 Hz, 2H); 4.51 (s, 2H); 6.92 (dt, J=9.1 Hz, 1H); 7.07-7.27 (m, 6H); 7.36 (dd, J=8.8 Hz, 1H); 10.74 (s, 1H). 13C-NMR (DMSO-d6): -5.2; 16.9; 23.9; 26.3; 31.5; 36.2; 36.5; 37.4; 57.1; 64.6; 75.2; 103.0 (d, J=23 Hz); 109.7 (d, J=27 Hz); 112.1 (d, J=11 Hz); 121.6 (d, J=5 Hz); 125.4; 127.6; 128.6; 130.5; 135.3; 136.0; 139.1; 156.7 (d, J=232 Hz).

The synthetic route of 61272-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUNENTHAL GMBH; US2009/215725; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 1000801-26-2, These common heterocyclic compound, 1000801-26-2, name is 4-(Difluoromethoxy)-2-iodoaniline, 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.

INTERMEDIATE 7 (METHOD H)fert-Butyl (35)-3-[3-(trimethylsilv?prop-2-vn- 1 -yllmophiholine-4-carboxylateTo a solution of Intermediate 6 (8.05 g, 35.7 mmol) dissolved in anhydrous THF (250 mL) at 00C was added n-butyllithium (15.7 mL, 39.3 mmol, 2.5 M in hexanes) dropwise over 15 minutes. After stirring for 30 minutes, chlorotrimethylsilane was added slowly over 5 minutes and the reaction mixture stirred for 45 minutes and then allowed to warm to r.t. After stirring at r.t. for 18 h, the reaction mixture was quenched by the addition of water (ca 1 mL) and the solvent was removed in vacuo. The crude mixture was dissolved in DCM and washed with water, the aqueous phase was extracted with further DCM (500 mL) and the combined organic fractions were dried using an Isolute phase separator cartridge and concentrated in vacuo to give a dark brown oil. Purification by column chromatography (SiO2, 5-20% EtOAc/hexanes) gave the title compound (8.1 g, 76%) as a colourless oil and recovered starting material (1.25 g, 15%). delta? (CD3OD) 3.91 (IH, m), 3.82 (IH, d, J 11.7 Hz), 3.70 (IH, dd, J 3.6 and J 11.4 Hz), 3.58 (IH, dd, J 2.9 and J 13.7 Hz), 3.40-3.20 (2H, m), 2.95 (IH, m), 2.60 (IH, dd, J9.1 and J 16.7 Hz), 2.38 (IH, dd, J6.4 and J 16.7 Hz), 1.35 (9H, s), 0.00 (9H, s).

The synthetic route of 1000801-26-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; WO2009/1089; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 191348-14-8, These common heterocyclic compound, 191348-14-8, name is 2-Iodo-4-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.

To a solution of 2-iodo-4-methoxyaniline 30-d ( 1.00 g, 4.02 mmol) in DMF cooled to 0C were sequentially added diethylamine (419 uL, 4.02 mmol), copper(I) iodide (143 mg, 0.80 mmol) and dichlorobis(triphenylphosphine) palladium (II) (282 mg, 0.40 mmol). After complete dissolution of copper(I)iodide, propyl 3,3-dimethylhex-5-ynoate 1 1-d (805 mg, 4.42 mmol) was added dropwise at 0C and the reaction was then stirred at room temperature overnight. Water and ethyl acetate were added; the organic layer was separated, washed with saturated aqueous ammonium chloride and brine, dried over anhydrous MgS04, filtered and concentrated in vacuo. Purification by silica gel chromatography provided intermediate 30-e as a beige oil. MS (m/z) M+H=304

The synthetic route of 191348-14-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMASCIENCE INC.; BUREAU, Patrick; FOURNIER, Jean-Hugues; JAQUITH, James B.; LAURENT, Alain; ROSE, Yannick; PROULX, Melanie; MORRIS, Stephen; WO2012/126084; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 89459-38-1,Some common heterocyclic compound, 89459-38-1, name is 2-Iodo-4-nitrobenzoic acid, molecular formula is C7H4INO4, 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 Example 2.140.1 (130 g) in a mixture of methanol (1000 mL) and sulfuric acid (23.65 mL) was stirred at 85 C. for 16 hours and concentrated to dryness. The residue was triturated with methanol (100 mL) and the suspension was stirred for 10 minutes. The solid was collected by filtration, washed with water (200 mL*3) and methanol (20 mL), and air-dried for 16 hours to give the title compound. MS (LC-MS) m/e 308.0 (M+H)+.

The synthetic route of 89459-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Benatuil, Lorenzo; Bruncko, Milan; Chao, Debra; Izeradjene, Kamel; Judd, Andrew S.; Phillips, Andrew C.; Souers, Andrew J.; Thakur, Archana; (556 pag.)US2017/355769; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 88-67-5, 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 88-67-5 as follows.

Prepared according to literature procedure. A solution of 2-iodobenzoic acid (1,240 mg, 5.0 mmol) in Conc. H2SO4 ( 10.00 mL) was heated at 60 C for 20 minutes. The solution was yellow orange. Then N-bromosuccinimide (1,668 mg, 6.0 mmol) was added in three portions each during 15 minutes. The mixture was brown and allowed to stir for 2 hours. After the reaction was completed, filtered and wash with cold water. A white solid was obtain. The aqueous eluted was extracted with EtOAc, the organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated that to obtain white solid. 1H NMR (300 MHz, CDCl3) delta 8.12 (d, J = 2.4 Hz, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.33 (dd, J = 8.4, 2.4 Hz, 1H); 13C NMR (75 MHz, CDCl3) delta 169.7, 143.2, 136.6, 134.9, 134.7, 122.4, 92.7. Other data was identical to the literature values.

According to the analysis of related databases, 88-67-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Duangjan, Chanikan; Rukachaisirikul, Vatcharin; Saithong, Saowanit; Kaeobamrung, Juthanat; Tetrahedron Letters; vol. 59; 39; (2018); p. 3537 – 3540;,
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. 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Product Details of 401-81-0

The N-nucleophile (2.21 mmol), Cu2O (Sigma-Aldrich, 99.99% purity, 0.147-0.294 mmol), K3PO4(2.94 mmol), the aryl halide (1.47 mmol), phase transfer catalyst (0.147-0.294 mmol) and water(0.40 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture wasstirred under air in a closed system at 130C for 24 h, then the heterogeneous mixture was cooledto RT and diluted with dichloromethane. The resulting solution was directly filtered through apad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solventwas removed under reduced pressure. The crude product was purified by silica-gel columnchromatography to afford the N-arylated product. The identity and purity of all products wasconfirmed by 1H and 13C NMR spectroscopic analysis.

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:
Article; Yong, Fui-Fong; Teo, Yong-Chua; Chua, Guan-Leong; Lim, Gina Shiyun; Lin, Yizhen; Tetrahedron Letters; vol. 52; 11; (2011); p. 1169 – 1172;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com