Iodides-buliding-blocks

Synthetic Route of 645-00-1,Some common heterocyclic compound, 645-00-1, name is 1-Iodo-3-nitrobenzene, molecular formula is C6H4INO2, 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: TAPEHA-Pd (0.015 g) was added to a solution of nitroarenes (1.0 mmol) in EtOH/water (1/1) (20 mL). After NaBH4 (4.0 mmol) was slowly added to the mixture, the color of the reaction mixture turned gradually black in a few minutes, resulting in the formation of palladium nanoparticles (TAPEHA-PdNPs). 42 After being stirredfor 1.5 h at room temperature and atmospheric pressure, the catalyst was removed by ltering and the fitrate was extracted with 3 30 mL of EtOAc. The combined organic layers were dried over MgSO4 and concentrated in a vacuum.

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-3-nitrobenzene, its application will become more common.

Reference:
Article; Genc, Hayriye; Zengin, Mustafa; Kuecuekislamo?lu, Mustafa; Imamoglu, Mustafa; Toplan, Hueseyin Oezkan; Arslan, Mustafa; Turkish Journal of Chemistry; vol. 41; 5; (2017); p. 784 – 792;,
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Electric Literature of 355-43-1, 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 355-43-1 as follows.

In a 25 mL round bottomed flask, was placed under N2 atmosphere a mixture of 2 (0.66 g, 2.0 mmol), perfluoro 1-iodohexane or perfluoro 1-iodooctane (2.5 mmol), AIBN (13 mg, 0.08 mmol) and 2 mL of 1,2-dichloroethane. The mixture was then stirred at 75C for 18 h. After cooling to room temperature, the solvent was removed under vacuum and the residue was subjected to a column chromatography on silica gel (ethyl acetate/hexane: 1/3) followed by a recrystallization in ethanol, to provide 3a and 3b as white solids. 4.3.1. 4′-{(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononyl)oxy}-(1,1′-biphenyl)-4-yl benzoate (3a) Yield: 89%. 1H NMR (CDCl3) d 8.25 (d, 2H, J = 7.5 Hz), 7.5-7.7 (m,7H), 7.30 (d, 2H, J = 8.2 Hz), 7.0 (d, 2H, J = 8.5 Hz), 4.55 (quint., 1H, CHI), 4.21-4.38 (dd, 2H,2J = 10.5 Hz,3J = 4.8 Hz, CHICH2O), 2.85-3.23 (m, 2H, CF2CH2CHI). 13C NMR (CDCl3) d(ppm) 165.2(CO), 157.2 (ArO), 150.1 (ArO), 138.3, 134.2, 133.6, 130.2, 129.51, 128.5, 128.3, 127.8, 121.9, 115.2, 72.8 (CH2O), 37.8 (t,2JCF= 21 Hz, CF2CH2), 12.7 (CI). 19F NMR (CDCl3) d(ppm) 80.5 (t, CF3, 3JFF= 10.0 Hz), 113.1 & 113.3 (dm & dm, 21F, JA-B= 295 Hz, 2 diastereoisomers of CHICH2CF2), 121.5 (m, 2F), 122.6 (m,2F), 123.3 (m, 2F), 125.8 (m, 2F). HRMS (ESI) calculated for C28H18F13IO3Na+: 799.314 (found: 799.005).

According to the analysis of related databases, 355-43-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Marzouk, Samir; Khalfallah, Ali; Heinrich, Benoit; Khiari, Jamel Eddine; Kriaa, Abdelkader; Mery, Stephane; Journal of Fluorine Chemistry; vol. 197; (2017); p. 15 – 23;,
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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. 354574-31-5, name is 2-Iodo-6-methoxyaniline, A new synthetic method of this compound is introduced below., Formula: C7H8INO

EXAMPLE 2 Total Synthesis of Azagalanthamine 2.1 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxyphenyl)acetamide (16); A solution of (1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid (567 mg; 2.86 mmol; 1 eq) (7) and 2-iodo-6-methoxyaniline (1 g; 2.86 mmol; 1 eq) in anhydrous dichloromethane (30 mL) is admixed with 2-chloro-1-methylpyridinium iodide (1.46 g; 5.73 mmol; 2 eq) and triethylamine (3.98 mL; 28.65 mmol; 10 eq). The reaction mixture is heated at reflux for 20 hours. After cooling and acidification with iN HCl solution to pH=5-6, the mixture is extracted with dichloro-methane. The organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated under vacuum. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6) gives 1.10 g of 2-(1,4-di-oxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide (16) in the form of a yellow foam (yield: 90%). Elemental analysis calculated for C17H20INO4 (m.p.: 429.25) C, 47.57; H, 4.70; N, 3.26; O, 14.91; found C, 47.39; H, 4.59; N, 3.01; O, 15.16. IR (CHCl3) nu (cm-1): 3382 (N-H); 1687 (CO) MS (ES) m/z: 429.8 [M+H]+. 1H NMR (CDCl3; 300 MHz) delta (ppm): 7.43 (dd, J=8.0, J=1.2; 1H; H3′); 7.18 (broad s; 1H; NH); 6.98 (t, J=8.0; 1H; H4′); 6.91 (dd, J=8.0, J=1.2; 1H; H5′); 5.72 (broad s; 1H; H4); 3.99 (s; 4H; Hdioxolane); 3.80 (s; 3H; OCH3); 3.15 (s; 2H; H2); 2.45 (broad s; 1H; H8); 2.37 (broad s; 1H; H5); 2.37 (broad s; 2H; H6); 1.85 (t, J=6.4; 2H; H7). 13C NMR (CDCl3; 62.9 MHz) delta (ppm): 169.2 (C(O)NH); 155.5 (C6′); 132.9 (Cl’); 130.8 (C3′); 129.6 (C4′); 128.1 (C8); 124.9 (C7); 111.7 (C5′); 107.7 (C5); 99.8 (C2′); 64.8 (Cdioxolane); 56.1 (OCH3); 45.7 (C2); 35.9 (C6); 38.2 (C4); 35.0 (C3).

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; Thal, Claude; Guillou, Catherine; Beunard, Jean-Luc; Gras, Emmanuel; Potier, Pierre; US2005/65338; (2005); A1;,
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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,
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Electric Literature of 811842-30-5, These common heterocyclic compound, 811842-30-5, name is 2-Bromo-1-fluoro-4-iodobenzene, 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.

Mix 2-bromo-1-fluoro-4-iodobenzene (18.0 g, 0.06 mol), Cu2O (36.0 mg, 0.25 mmol), and KOH (5.6 g, 0.10 mol) in 1,4-dioxane (20 ml) ), Under the protection of nitrogen, cyclopentathiol (5.1 g, 0.05 mol) was added to the system through a syringe, and the temperature was raised to 110 C. for overnight reaction. After the reaction solution was cooled to room temperature, ethyl acetate (30 ml) was added, and the filter cake was washed with ethyl acetate (20 ml). The filtrates were combined and concentrated to dryness under reduced pressure. The residue was separated by column chromatography to obtain the title compound (12.0 g, yield 72%).[1283]1H NMR (400MHz, CDCl 3) delta 7.62-7.49 (m, 1H), 7.34-7.20 (m, 1H), 7.09-6.95 (m, 1H), 3.52 (td, J = 7.2, 3.6Hz, 1H) , 2.08–1.92 (m, 2H), 1.85–1.56 (m, 6H).

The synthetic route of 811842-30-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JIANGSU HANSOH PHARMACEUTICAL GROUP CO., LTD.; SHANGHAI HANSOH BIOMEDICAL CO., LTD.; SU, Yidong; GU, Peng; CHEN, Xiaopo; LIU, Lei; BAO, Rudi; (192 pag.)WO2018/130174; (2018); A1;,
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These common heterocyclic compound, 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, 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. Recommanded Product: 689291-89-2

To an oven-dried flask protected under a N2 atmosphere were charged compound 12 (540 mg, 1.74 mmol), trimethylsilylacetylene (0.68 g, 6.9 mmol), PdCl2(PPh3)2 (60 mg, 0.085 mmol), CuI (30 mg, 0.16 mmol), and Et3N (10 mL). The solution was bubbled by N2 at rt for 5 min and then heated to 60 C under stirring and N2 protection overnight. After the reaction was complete as checked by TLC analysis, the solvent was removed by rotary evaporation. The resulting residue was diluted with CHCl3. The mixture was filtered through a MgSO4 pad. The solution obtained was sequentially washed with HCl (aq. 10%) and brine. The organic layer was dried over MgSO4 and concentrated under vacuum to give crude 20, which was further purified by silica flash column chromatography (hexanes/CH2Cl2, 4:1) to yield compound 20 (518 mg, 1.74 mmol, 100%) as a colorless oil.

The synthetic route of 5-Bromo-2-iodobenzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Ningzhang; Wang, Li; Thompson, David W.; Zhao, Yuming; Tetrahedron; vol. 67; 1; (2011); p. 125 – 143;,
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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;,
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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,
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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,
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Some common heterocyclic compound, 17024-12-3, name is 9-Iodophenanthrene, molecular formula is C14H9I, 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: C14H9I

Mixed under argon flow were 100 g of N,N’-diacetyl-4,4′-benzidine (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 337 g of 9-iodophenanthrene, 204 g of anhydrous potassium carbonate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 4.7 g of copper powder (manufactured by Hiroshima Wako Co., Ltd.) and 750 ml of decalin, and they were reacted at 190C for 3 days. After cooling, 2 liter of toluene was added thereto to filter an insoluble matter. The matter filtered was dissolved in 4.5 liter of chloroform to filter off an insoluble matter, and then the filtrate was treated with activated carbon and concentrated under reduced pressure. Acetone 3 litter was added when the solution became slurry in the middle of concentration, and crystal deposited was filtered and dried. This was suspended in a mixture of 2 liter of ethylene glycol and 20 ml of water, and 110 g of a 85 % potassium hydroxide aqueous solution was added thereto, followed by carrying out reaction at 120C for 12 hours. After left cooling down to a room temperature, the reaction liquid was injected to 4 liter of water and treated with activated carbon, and then it was concentrated under reduced pressure. Acetone was added when the solution became slurry, and crystal deposited was filtered and dried to obtain 116 g of N,N’-bis(phenantho-9-yl)-4,4′-benzidine (A3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17024-12-3, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1559706; (2005); A1;,
Iodide – Wikipedia,
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