Iodides-buliding-blocks

Synthetic Route of 626-44-8,Some common heterocyclic compound, 626-44-8, name is 1,3,5-Triiodobenzene, molecular formula is C6H3I3, 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 1,3,5-triiodobenzene (0.46 g, 1.0 mmol), diphenylphosphine oxide (0.73 g, 3.6 mmol), CuI (0.06 g, 0.30 mmol), l-proline (0.04 g, 0.30 mmol), and Cs2CO3 (1.5 g, 4.5 mmol) was added to toluene solution (30 mL). The mixture was refluxed under nitrogen for 48 h. After the reaction finished, the reaction mixture was extracted with dichloromethane and washed with water. The organic layer was dried by anhydrous MgSO4 and filtered. The product was isolated by silica gel column chromatography using methanol/ethyl acetate (1:5) as eluent to afford a white solid (0.64, 52%). 1H NMR (300 MHz, CDCl3, delta): 8.08 (t, J = 11.9 Hz, 3H), 7.52 (dd, J = 12.9, 7.2 Hz, 18H), 7.39 (dd, J = 9.8, 4.8 Hz, 12H). 13C NMR (75 MHz, CDCl3, delta): 141.05, 141.02, 140.91, 134.89, 134.66, 134.39, 133.00, 131.36, 131.19, 31P NMR (121 MHz, CDCl3, delta): 27.59. HRMS [m/z]: calcd for C42H33O3P3, 678.1643; found, 679.1711 [M+H+]. Anal. Calcd. for C42H33O3P3: C, 74.33; H, 4.90. Found: C, 74.36; H, 4.88.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3,5-Triiodobenzene, its application will become more common.

Reference:
Article; Ban, Xinxin; Sun, Kaiyong; Sun, Yueming; Huang, Bin; Jiang, Wei; Organic electronics; vol. 33; (2016); p. 9 – 14;,
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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 146137-72-6 as follows. Recommanded Product: 146137-72-6

General procedure: To a solution of the aldehyde 1aev (1 eq.) in tert-butanol(9.0 ml/mmol) the diamine (1.1 eq.)was added and the solutionwasstirred at 70 C for 30 min K2CO3 (4 eq.) and I2 (1.25 eq.) was addedat 70 C and the mixture was stirred at this temperature for further3 h. The mixture was cooled down to rt and Na2S2O3 was addeduntil the iodine color almost disappear. The organic layer wasseparated and the solvent was removed in vacuo. The received solid was dissolved in water (7.5 ml/mmol) and 2 N NaOHaq was addeduntil pH 12e14. The aqueous layer was separated with CHCl3(3 3.75 ml/mmol), the combined organic layers were dried(Na2SO4) and the solvent was removed in vacuo. The product can beused without further purification.

According to the analysis of related databases, 146137-72-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wolff, Benjamin; Jaensch, Niklas; Sugiarto, Wisely Oki; Fruehschulz, Stefan; Lang, Maraike; Altintas, Rabia; Oehme, Ina; Meyer-Almes, Franz-Josef; European Journal of Medicinal Chemistry; vol. 184; (2019);,
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Application of 401-81-0, 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. 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Catalyst 2c (prepared according Ref. 26b, 133 mg, 6.2 equiv of Pd) was added to a solution of aryl iodide (0.20 mmol, 1.0 m equiv), alkene (0.40 mmol, 2.0 equiv) in DMF (2 mL). The reaction mixture was heated at 100 C for 20 h. After cooling to rt, compound 2c was filtered off under vacuum using a 0.2 mum membrane. The mixture of solvents was concentrated under vacuum to afford pure 3a-j after drying under vacuum (0.1 mbar). The catalyst 2c was then regenerated by reaction with NBu3 (0.16 mL, 0.66 mmol, 3.3 equiv) in DMF at rt for 3 h. Compound 2c was then filtered under vacuum, washed with Et2O (2 mL), and dried under vacuum.

The synthetic route of 1-Iodo-3-(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Derible, Antoine; Yang, Yun-Chin; Toy, Patrick H.; Becht, Jean-Michel; Le Drian, Claude; Tetrahedron Letters; vol. 55; 31; (2014); p. 4331 – 4333;,
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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 173406-17-2 as follows. Recommanded Product: 173406-17-2

To a mixture of 244 mg of 3- (2-aminoetliyl) pyridine (2.0 mmol) and 604 mg of t-butyl 3- iodobenzoate (2.0 mmol) in 10 [ML] of toluene was added 250 mg of sodium t-butoxid (2.5 [MMOL),] 30 mg [OF TRI-T-BUTYLPHOSPLIONIMN TETAFLUOROBORATE] (0.1 mmol) and 50 mg of tris (dibenzylidineacetone) dipalladium [(0)] (0.055 [MMOL).] The mixture was stirred for 16 h and filtered through celite. The celite was washed with 3 X 5 mL of toluene and the filtrate was concentrated in vacuo. The residue was purified by column [CHROMATOGRAPHY] using 35%-45% EtOAc in hexanes as eluant to give 103 mg of t-butyl N- (2- (3-pyridyl) ethyl)-3-aminobenzoate as a bright yellow oil (17% yield).

According to the analysis of related databases, 173406-17-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2004/9552; (2004); A1;,
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Some common heterocyclic compound, 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, molecular formula is C8H9I, 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. Computed Properties of C8H9I

To a solution of 1-iodo-2,3- dimethylbenzene (8) [prepared according to Chen, Y et al. Org. Lett. 2007, 9, 1899] (1 .93 g, 8.32 mmol) in carbon tetrachloride (40 mL) was added NBS (3.67 g, 20.62 mmol), AIBN (0.070 g, 0.43 mmol) and the resulting mixture was gently refluxed by irradiation with a halogen lamp (500 W) for 4 h. The precipitate was filtered and washed with a small amount of carbon tetrachloride. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc ( 1 00 ml), successively washed with 10% NaOH solution (20 mL), water (2 x 20 ml), 10% Na2S203 solution (20 mL), water (20 mL), brine (20 raL), and dried (Na2SC>4). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether) to give 1 .89 g (58.3%) of compound 9. NMR (CDC13) delta: 7.84 (dd, J=8.1 , 1 .1 Hz, 1 H), 7.33 (dd, J=7.6, 1 .1 Hz, l H), 6.97 (t, J=7.8 Hz, 1 H), 4.85 (s, 2H), 4.66 (s, 2H). The product contained ca. 15-20% of an inseparable impurity (supposedly l -bromo-2,3-bis(bromomethyl)benzene).A mixture of 1,2-bis(bromomethyl)-3-iodobenzene (9) (2.50 g, 6.41 mmol), diethyl 2-acetamidomalonate (1 .39 g, 6.41 mmol), and K2C03 (2.22 g, 1 6.06 mmol) in acetonitrile (40 mL) was refluxed for 70 h. The mixture was allowed to cool to ambient temperature, the precipitate was filtered and washed with a small amount of acetonitrile. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc (100 mL), washed successively with saturated NaHC03 solution (30 mL), water (2 x 30 mL), brine (30 mL), and dried (Na2S04). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 2 g of oil. The oil was dissolved in diethyl ether and kept in a refrigerator overnight. The precipitate was filtered and dried to give 0.4 g (14%) of a regioisomer diethyl 2-acetyl-5-iodo-l ,4-dihydroisoquinoline-3,3(2H)-dicarboxylate. NMR (CDC13) delta: 7.76 (d, J=8.0 Hz, 1H), 7.13 (d, J=7.5 Hz, 1 H), 6.94 (t, J = 7.7 Hz, 1H), 4.65 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 4.16 (q, J=7.1 Hz, 2H), 3.56 (s, 2H), 2.28 (s, 3H), 1 .22 (t, J=7.1 Hz, 3H), 1.22 (t, J=7.1 Hz, 3H). LCMS (ESI) m/z: 446 [M+H]+. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 0.95 g (33.2%) of compound (10).A solution of diethyl 2-acetyl-8-iodo-l,4-dihydroisoquinoline-3,3(2H)-dicarboxylate (10) (0.585 mmol) in 6 N HQ (10 mL) was refluxed for 5 h. The mixture was cooled and cone. NH4OH water solution was added until pH of the medium was ~7. The precipitate was filtered, washed with a small amount of water, and dried to give 0.305 g (76.7%) of compound (11). Because of a low solubility of the product in common deuterated organic solvents and deuterium oxide, the NMR spectrum was not informative. LCMS (ESI) m/z: 304 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid). LCMS (ESI) m/z: 256 [M+H]+.To a suspension of 8-iodo-l ,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (11) (0.645 g, 2.13 mmol) in methanol ( 1 8 mL) slowly SOCI2 ( 1.07 ml, 14.92 mmol) was added within 10 min. The reaction mixture was stirred at room temperature for 16 h, evaporated, and the residue was dissolved in a mixture of IN NaHC03 solution (30 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 ^ 15 mL). The organic extracts were combined, washed successively with water (20 mL), brine (20 mL), and dried (Na2S04). The solvents were evaporated to give compound 12 (0.570 g, 84%) which was used in the next step without further purification. NMR (CDCI3) delta: 7.67 (d, J=7.8 Hz, IH), 7.10 (d, J=7.5 Hz, I H), 6.87 (t, J=7.7 Hz, IH), 4.07 (d, 16.6 Hz, IH), 3.87 (d, J=16.6 Hz, I H), 3.78 (s, 3H), 3.71 (dd, J=9.4, 5.0 Hz, I H), 3.04 (dd, J=16.5, 5.0 Hz, IH), 2.97 (dd, J=l 6.5, 9.4 Hz, IH). LCMS (ESI) m/z: 318 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative methyl 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate). LCMS (ESI) m/z: 270 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 31599-60-7, its application will become more common.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; JIRGENSONS, Aigars; LOZA, Einars; CHARLTON, Michael; FINN, Paul William; RIBAS DE POUPLANA, Lluis; SAINT-LEGER, Adelaide; (76 pag.)WO2016/129983; (2016); A1;,
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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. 25245-29-8, name is 5-Iodo-1,2,3-trimethoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C9H11IO3

Step 1: 2-(3,4,5-Trimethoxy-phenyl)-2,3-dihydro-furan (287) To a solution of 5-iodo-1,2,3-trimethoxybenzene (900 mg, 3.06 mmol) and 2,3-dihydrofuran (1.16 mL, 15.3 mmol) in dry DMF (8 mL) were added PPh3 (20 mg, 0.077 mmol), KOAc (901 mg, 9.18 mmol), n-Bu4NCl (850 mg, 3.06 mmol) and Pd(OAc)2 (17 mg, 0.077 mmol). The reaction mixture was stirred 18 h at 80 C. The reaction mixture was diluted with AcOEt and water. After separation, the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/Hexane: 20/80) to afford the title compound 287 (311 mg, 1.32 mmol, 43% yield). 1H NMR: (300 MHz, CDCl3) delta (ppm): 6.59 (s, 2H), 6.45 (m, 1H), 5.45 (dd, J=10.5, 8.4 Hz, 1H), 4.97 (m, 1H), 3.87 (s, 6H), 3.84 (s, 3H), 3.06 (m, 1H), 2.62 (m, 1H).

The synthetic route of 25245-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MethylGene, Inc.; US2004/142953; (2004); A1;; ; Patent; MethylGene, Inc.; US6897220; (2005); B2;,
Iodide – Wikipedia,
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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. 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, This compound has unique chemical properties. The synthetic route is as follows., category: iodides-buliding-blocks

The reference gathers the precedent 11 the obtained 1 – [trans-4 – (hydroxy methyl) cyclohexyl] – 3,7-bis-{ [2 – (trimethyl silicon alkyl) ethoxy] methyl} – 1H-pyrrolo [3 ‘, 2’ : 5,6] pyrido [4,3-d] pyrimidine -2,4 (3H, 7H)-dione (1.35g, 2 . 35mmol) bis methyl chloride (14 ml) is added in the solution 1, 1, 1-trifluoro-3- propyl iodide (1.34 ml, 11 . 8mmol), 2,6-di-tert-butyl pyridine (2.38 ml, 10 . 8mmol) and trifluoro methane sulfonic acid silver (2.60g, 10 . 1mmol), stirring 113 hours. Furthermore, filter the reaction mixture, added to the resulting filtrate extraction of chloroform and water. The resulting organic layer after drying with anhydrous sodium sulfate, concentrated under reduced pressure. Residues to silica gel column chromatography (section 1 time: hexane/ethyl acetate = 1/0 ? 78/22(v/v), paragraph 2 time: hexane/ethyl acetate = 1/0 ? 4/1(v/v), paragraph 3 time: hexane/ethyl acetate = 1/0 ? 4/1(v/v)) purification of 3 time, to obtain the colorless amorphous title compound (1.34g, yield 85%).

According to the analysis of related databases, 460-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; WATANABE, TSUNEO; TAKAHASHI, KEIJI; HAYASHI, KEISHI; NAKAMURA, TAKANORI; MINAMI, MASATAKA; KURIHARA, KAZUNORI; YAMAMOTO, AKIO; NISHIMURA, TAKUYA; UNI, MIYUKI; KAMIYAMA, TOSHIHIKO; IWAMOTO, SHUNSUKE; (96 pag.)TW2016/7947; (2016); A;,
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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. 29632-73-3, name is 2-Bromo-4-iodoaniline, A new synthetic method of this compound is introduced below., Computed Properties of C6H5BrIN

To a solution of (10) (570 mg, 1.9 mmol) in dry toluene (8 mL), was added PPh3 (65.5 mg, 0.2 mmol) and Pd(OAc)2 (47.5 %, 60 mg, 0.1 mmol). tert-Butyl Acrylate (370 mu., 2.5 mmol) and NEt3 (420 mu., 3.0 mmol) were added and the flask was stirred at reflux overnight. The reaction was allowed to cool and washed with saturated aqueous NH4C1, brine, extracted with DCM, dried (Na2S04), filtered and concentrated. Purification by column chromatography (Hexane:EtOAc = 12: 1, 9: 1, 4: 1) provided the title compound as a brown oil (238.5 mg, 0.8 mmol, 64 %) Rf : 0.23 (Hexane:EtOAc, 4: 1). 1H NMR (400 MHz; CDC13,): delta 1.51 (9H, s, C(CH3)3), 6.15 (1H, d, J = 15.8 Hz, CH), 6.69 (1H, d, J = 8.1Hz, ArCH), 7.23 (1H, d, J = 8.2 Hz, ArCH), 7.40 (1H, d, J = 15.8 Hz, CH), 7.55 (1H, s, ArCH). 13C NMR (100 MHz; CDC13,): delta 28.2, 80.2, 109.0, 115.3, 117.0, 126.0, 128.4, 132.4, 142.3, 145.7, 166.6.

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; TEXAS TECH UNIVERSITY SYSTEM; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; TRIPPIER, Paul; VERMA, Kshitij; PENNING, Trevor, M.; ZHANG, Tianzhu; (204 pag.)WO2018/148721; (2018); A1;,
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Some common heterocyclic compound, 1450754-38-7, name is 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine, molecular formula is C7H9IN2, 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. Quality Control of 3-(But-3-yn-1-yl)-3-(2-iodoethyl)-3H-diazirine

A mixture of compound S4 (90.0 mg, 286 lirnol, I equiv), and iodo-diazirine S7 (70.0 mg, 286 imol, 1.00 equiv) was dissolved in DMF (3.0 rnL) at 24 C. To this mixture, was added potassium carbonate (40.0 mg, 286 umol, 100 equiv) and stirred for 12 hours at 24 C. The reaction mixture was partitioned between ethyl acetate (30 mL) and DI water (15 mL) and the organic portion was separated and washed with brine (3 x 15 mL). The combined organic portion was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford an off white powder. The powder was purified by flash column chromatography (30—60% ethyl acetate–hexane, three steps) to afford photo-celecoxib (5) as a white powder (92.0 nig, 75Rf = 0.20 (40% ethyl acetate—hexane; UV). ?H NMR (500 MHz, CDCI3): oe 8.05 (d, 21-1, J 8.2 Hz, H3). 8.02 (d, 2H, J 8.1 Hz, Fl4), 5.95 (s, iH, H?), 5.13 (br, 2H, H5), 4.04 (t,21-1, J 7.2 Hz, H2). 2.05—2.03 (in, 51-1, E-16/I-18/H9), i.71—i.69 (in, 21-1. H7). ?3C N]?[R (125 MIz, CDCI3): d 154.6 (C), 143.0 (q, 2JCF = 38.8 Hz, CH), 141.1 (C), 140.4 (C), 127.6 (CH), 122.5 ((1-1), 121.7 (q, IJCF 267.5 Hz CF3), 5.3 (C), 82.4 (C), 69.7 (CH). 67.6 (OCH2),32.4 (CH2), 32.1 (CH2), 26.1 (CN2), 13.2 (CH3). ?9FvR(375 MHz, CDCI3): -63.6. IR (ATR-FT1R), cnf?: 3277 (br), 1590 (s), 1563 (m), 1512 (m), 1490 (w), 1416 (m), 1380 (w), 1335 (w), 1246 (m), 1151 (rn), 1101 (rn), 968 (w), 908 (w), 40 (w), 743 (w), 715 (w), 626 (in), 543 (w). HRMS-ES1 (m/z): [M+F1] calculated for Ci7H,7F3NsO3S, 428,0999; found,428.0949.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1450754-38-7, its application will become more common.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; WOO, Christina, M.; GAO, Jinxu; (555 pag.)WO2018/226828; (2018); A2;,
Iodide – Wikipedia,
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Some common heterocyclic compound, 63069-48-7, name is 4-Chloro-2-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. Product Details of 63069-48-7

Step A: Preparation of l -Bromo-4-chloro-2-iodobcnzenc; |0892 ] A stirred mixture of coppcr(l l) bromide ( 1 1 mL, 237 mmol) in250 mL ACN at O0C was slowly treated with tert-butyl nitrite (33 mL, 276 mmol). The mixture was then warmed to 65C. and stirred for 30 minutes. The mixture was next treated dropwise with a mixture of 4-chloro-2-iodoaniline (50 g, 197 mmol) in 100 mL ACN. The resulting mixture was stirred for 1 hour. The mixture was cooled to room temperature and poured over 200 mL ice/10%HCl. The mixture was extracted with ether (3 x 100 mL). The combined organic layers were washed with I hO (2 100 m l .). 1 % ammonia water (2 x 100 niL), brine ( 100 ml), dried over anhydrous Na2SOi. and concentrated in vacuo to give 63 g brown oil as crude product. The crude product was purified by running it through a short silica plug eluting with 5% ether / hexane to give 54.2 g of the title compound 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 63069-48-7, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2008/76427; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com