Month: February 2021

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;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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;,
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. 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,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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;,
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. 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;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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

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. 628-77-3, name is 1,5-Diiodopentane, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H10I2

A solution of Compound 33 (50.0 mg, 0.20 mmol) in DMF (5.0 mL) was added K2CO3 (42.26 mg, 0.31 mmol) and 1,5-diiodopentane (333 mg, 1.0 mmol). The reaction mixture was stirred at 90 C. for 3 h. The reaction mixture was purified by silica chromatography (0-50% EtOAC in petroleum ether) to give (S)-8-((5-hydroxypentyl)oxy)-7-methoxy-1,2,3,11a-tetrahydro-5H-benzo[e]pyrrolo[1,2-a]azepin-5-one 34 (60 mg, 0.178 mmol, 87.6% yield) as an oil. LCMS (5-95AB/1.5 min): RT=0.765 min, [M+H]+ 332.0

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 628-77-3.

Reference:
Patent; Genentech, Inc.; Dragovich, Peter; Pillow, Thomas; Sadowsky, Jack; Sliwkowski, Mark X.; Wei, BinQing; (160 pag.)US2017/95570; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 672-57-1, The chemical industry reduces the impact on the environment during synthesis 672-57-1, name is 1-Chloro-2-iodo-4-(trifluoromethyl)benzene, I believe this compound will play a more active role in future production and life.

4-Chloro-3-iodobenzenetrifluoride (306 mg) was dissolved in toluene (3 ml), and thereto were added 2-ethynylpyridine (155 mg), copper iodide (19.0 mg), 1,3-bis-(2,6-diisopropylphenyl)-imidazolium chloride (42.5 mg), acetic acid palladium (II) (22.5 mg) and cesium carbonate (489 mg), and the mixture was heated to 100 C. After the mixture was stirred for 3 h, the mixture was kept standing to cool to room temperature, and thereto were added 3-amino-6-methoxypyridine (149 mg) and potassium-t-butoxide (168 mg), and the reaction mixture was heated to 100 C. After the reaction mixture was stirred all day and all night, it was kept standing to cool to room temperature, and to the reaction solution were added ethyl acetate and water. After an insoluble material was filtrated, the organic layer was separated. The organic layer was washed with a saturated saline and dried with anhydrous sodium sulfate. After the organic layer was filtrated and concentrated, the residue was purified by the silica gel column chromatography affording the compound 2 (77.0 mg).MS m/z 370 [M+H]+, APCI(+)

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-Chloro-2-iodo-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsubishi Tanage Pharma Corporation; US2012/258951; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 6326-42-7, name is Methyl 2-iodo-4-nitrobenzoate, 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 6326-42-7, SDS of cas: 6326-42-7

[0001173] To a mixture of ammonium chloride (122 g) and iron (38.2 g) in ethanol (1000 mL) and water (100 mL) was added Example 2.140.2 (70 g,) at room temperature. The mixture was stirred at 80 C for 4 hours and filtered to remove insoluble material. The filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (1000 mL) and washed with water (500 mL). The aqueous phase was extracted with ethyl acetate (1000 mL x 2). The combined organic phase was washed with brine, dried over MgSO/i, filtered and concentrated to give the title compound. MS (LC-MS) m/e 278.0 (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, Methyl 2-iodo-4-nitrobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; TAO, Zhi-Fu; DOHERTY, George; WANG, Xilu; SULLIVAN, Gerard M.; SONG, Xiaohong; KUNZER, Aaron R.; WENDT, Michael D.; MARIN, Violeta L.; FREY, Robin R.; CULLEN, Steve C.; WELCH, Dennie S.; SHEN, Xiaoqiang; BENNETT, Nathan B.; HAIGHT, Anthony R.; ACKLER, Scott L.; BOGHAERT, Erwin R.; SOUERS, Andrew J.; JUDD, Andrew S.; (623 pag.)WO2016/94509; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com