Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 58313-23-8, name is Ethyl-3-iodobenzoate, 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 58313-23-8, Safety of Ethyl-3-iodobenzoate

General procedure: DIPEA (6 equiv) was added to a solution of propargylamine 7 (1 equiv) and the methyliodo-benzoate derivative (1.6 equiv) in THF (THF/DIPEA = 3:1). The reaction mixture wasdegassed by freeze pump thaw method, until no more gas atmosphere could be detected bythe manometer. The catalysts, Cl2Pd(PPh3)2 (2 mol %) and CuI (1 mol %) were added to thefrozen reaction mixture and the solution slowly warmed to room temperature. After 30-120 min, a colourless precipitate formed in the clear solution, indicating the progress of thereaction. At least 2-8 h later, the suspension was diluted with a saturated aqueous NH4Clsolution and KHSO4 (aq, 5 %) was added, until the organic layer started to turn faintly red(pH 5-6). The emulsion was diluted with Et2O, the organic layer separated and the organiclayer extracted to more times with Et2O. The combined organic layers were dried overNa2SO4 and the solvent was evaporated in vacuum. The crude product was purified bycolumn chromatography. Typical reactions were carried out on a scale of 0.1-0.5 g ofpropargylamine 7. Similar reactions have already been described by Hashmi [20], Ishida [21]and Wong et al. [22].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl-3-iodobenzoate, and friends who are interested can also refer to it.

Reference:
Article; Wuensch, Matthias; Schroeder, David; Froehr, Tanja; Teichmann, Lisa; Hedwig, Sebastian; Janson, Nils; Belu, Clara; Simon, Jasmin; Heidemeyer, Shari; Holtkamp, Philipp; Rudlof, Jens; Klemme, Lennard; Hinzmann, Alessa; Neumann, Beate; Stammler, Hans-Georg; Sewald, Norbert; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 2428 – 2441;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 628-77-3, name is 1,5-Diiodopentane, 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: 628-77-3

EXAMPLE 1 N, N’-Pentane-1, 5-diyl-bis-pyridinium Diiodide (bPPeI).; 1,5-Diiodopentane (mmol) was added to a solution (30 mL) of dry pyridine, and the solution heated for 24 hours at 65C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting yellow solid was isolated in a 90% yield. ‘H NMR (300 MHz, DMSO-D6) 8 9.14 (2H, d, C2&C6-H), 8.62 (1H, t, C4-H), 8.19 (2H, t, C3&C5-H), 4.62 (2H, t, C’1-CH2), 1.92 (2H, m, C’2-CH2), 1.25 (1H, m, C’3-CH2).

The synthetic route of 1,5-Diiodopentane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; WO2005/66129; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 167479-01-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 167479-01-8 name is tert-Butyl (3-iodopropyl)carbamate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 76 Preparation of N-[1-(3-tert-butoxycarbonylaminopropyl)-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N’-(2,6-diisopropylphenyl)urea STR91 The title compound was obtained in the same manner as in Example 58 from N-[4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N’-(2,6-diisopropylphenyl)urea and 3-tert-butoxycarbonylaminopropyl iodide. 1 H-NMR delta (CD3 OD) 8.64 (1H, dd, J=5.0 Hz, 1.7 Hz), 7.77 (1H, dd, J=8.3 Hz, 1.7 Hz), 7.49 (1H, dd, J=8.3 Hz, 7.6 Hz), 6.95-7.35 (7H, m), 4.74 (2H, t, J=6.9 Hz), 3.87 (3H, s), 3.20 (2H, t, J=6.6 Hz), 2.95-3.10 (2H, m), 1.90-2.10 (2H, m), 1.49 (9H, s), 1.15 (12H, brd, J=6.3 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (3-iodopropyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Ltd.; US5843957; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 444-29-1,Some common heterocyclic compound, 444-29-1, name is 1-Iodo-2-(trifluoromethyl)benzene, molecular formula is C7H4F3I, 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: In a typical experiment, the isolated crystalline precatalyst 1A (or 2A, 0.005 mmol) was sequentially mixed with 3 mL of solvent (DMF or [Bmim]PF6 if required), iodobenzene (5mmol), phenylacetylene (6 mmol), and Et3N (7.5 mmol). The obtained mixture was placed in a sealed Teflon?lined stainless steel autoclave, purged with syngas (CO, 1.0 MPa) and then stirred vigorously at the required temperature for the appointed time. Upon completion of the reaction, the mixture wasc ooled to room temperature and the pressure was carefully released. The reaction mixture was extracted with diethyl ether(5 mL 3). The ether fractions were combined and then analyzedby GC to determine the conversion of PhI (1?dodecane as an internal standard) and the selectivity for the carbonylative products (normalization method). The structures of the carbonylative products were further confirmed by GC?MS.

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-2-(trifluoromethyl)benzene, its application will become more common.

Reference:
Article; Yang, Da; Wang, Dongliang; Liu, Huan; Zhao, Xiaoli; Lu, Yong; Lai, Shijun; Liu, Ye; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 37; 3; (2016); p. 405 – 411;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 628-21-7,Some common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, molecular formula is C4H8I2, 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.

With reference to the above reaction formula 12, the ICH2CH2CH2CH2I (309 mg, 0 . 18mmol) containing as added to the starting material of the amine compound (amine compound, 40 mg, 0 . 15mmol), K2CO3(62 mg, 0 . 45mmol) of DMF (10 ml) solution, in 60 C mix 48 hours for reaction. Thus-prepared reaction solution, with the ice water (10 ml) after mixing, using CH2Cl2(2×20 ml) to carry out extraction. Collecting the organic layer, water (2x 10 ml) after washing, the use of non-aqueous sulfuric acid drying, to chromatographic method for the brown residue (CH2Cl2As eluant) is purified, thereby obtaining the chemical formula 27 compound (yield: 17 mg, 35%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Diiodobutane, its application will become more common.

Reference:
Patent; Shuntian Township University-Industry Association; Korea Chemical Research Institute; Song, Honyeon; Jang, Ungsig; Nam, Gungu; Li, Byeongui; Gil, Yeonsig; Li, Qiin; Sadu, Bunjabtab Seopaila; Jo, Huiyeong; (35 pag.)CN106176709; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 116632-39-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 116632-39-4 name is 5-Bromo-2-iodotoluene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Barium hydroxide monohydrate (2.27 g, 2.0 equiv), 4-bromo-1-iodo-2-methylbenzene (0.94 mL, 1.1 equiv), 3-chlorophenyl boronic acid (0.94 g, 1.0 equiv), and palladium tetrakis(triphenylphosphine) (0.14 g, 0.02 equiv) were combined and stirred in dioxane (15 mL) and water (5 mL), heated at reflux for 2 hr and then allowed to cool to room temperature. The solution was concentrated and the residue dissolved in CH2Cl2, washed with water and brine and then dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (SiO2, hexane) to give 4-bromo-3′-chloro-2-methyl biphenyl (0.33 g, 21%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-iodotoluene, and friends who are interested can also refer to it.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2004/82779; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 98-61-3, name is 4-Iodobenzenesulfonyl chloride, molecular formula is C6H4ClIO2S, 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. Safety of 4-Iodobenzenesulfonyl chloride

General procedure: To the solution of meridianin G (7) or meridianin C (3) indichloromethane (5 ml) was added DMAP (0.05 equiv.), aryl/heteroarylsulfonyl chloride (1.1 equiv.) and N,N-diisopropylethylamine(1.5 equiv.). The mixturewas stirred at room temperature for20 h. Reaction was then quenched by the addition of 10% HCl. Thisreaction mixture was extracted with dichloromethane (50 ml 3),and combined organic layer was evaporated on rotary evaporator.Purification by silica gel column chromatography (mesh 100e200)using dichloromethane-methanol (99:1 to 97:3) to get the titledproducts 14aead.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 98-61-3, its application will become more common.

Reference:
Article; Yadav, Rammohan R.; Khan, Shabana I.; Singh, Samsher; Khan, Inshad A.; Vishwakarma, Ram A.; Bharate, Sandip B.; European Journal of Medicinal Chemistry; vol. 98; (2015); p. 160 – 169;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 452-82-4,Some common heterocyclic compound, 452-82-4, name is 1-Fluoro-2-iodo-4-methylbenzene, molecular formula is C7H6FI, 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.

Example 2: 4-(Bromomethyl)-l-fluoro-2-iodobenzene Int-10 Step 1: 4-(Bromomethyl)-l-fluoro-2-iodobenzene Int-10 A mixture of 4-fluoro-3-iodotoluene (5 g, 21 mmol), NBS (3.77 g, 21 mmol) and azobisisobutyronitrile (35 mg, 0.21 mmol) in CC14 (30 mL) was heated to reflux for 4 h. The reaction was cooled to rt and concentrated. The residue was purified on silica gel to obtain 4-(bromomethyl)-l-fluoro- 2-iodobenzene (1.7 g, 26%). ‘HNMR (CDC13) delta 7.78 – 7.80 (m, IH), 7.32 – 7.37 (m, IH), 7.00 – 7.05 (m, IH), 4.41 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Fluoro-2-iodo-4-methylbenzene, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
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. 13421-13-1, name is 4-Chloro-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., Computed Properties of C7H4ClIO2

General procedure: To an oven dried three neck RB containing 2-Iodobenzoic acid (1) (2mmol), benzyl amine (2) (4mmol) and CuI(0.4mmol) in DMSO(3ml) was added 0.55g of K2CO3. Then, the reaction mixture was allowed to stir at 90C under air atmosphere for 12h.The completion of the reaction was monitored by TLC. After being cooled at room temperature the reaction mixture was poured in to ice cooled water and extracted with ethyl acetate two times. The combined organic layer was washed with brine and then dried over anhydrous Na2SO4. The solvent was evaporated and the crude product was purified by column chromatography (hexane(80)/ ethyl acetate (20)) on silica gel to afford 2-phenyl-4H-benzo[d][1,3]oxazine-4-one.

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; Munusamy, Sathishkumar; Venkatesan, Sathesh; Sathiyanarayanan, Kulathu Iyer; Tetrahedron Letters; vol. 56; 1; (2015); p. 203 – 205;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 289039-83-4, 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. 289039-83-4, name is Methyl 2-amino-5-bromo-3-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 2-amino-5-bromo-3-iodobenzoate (7.47 g, 20.99 mmol) in TEA (40 mL, 287 mmol) is added Pd(PPh3)2C12 (0.884 g, 1 .259 mmol), and copper(l) iodide (0.240 g, 1.259 mmol). The mixture is stirred under N2 for about 5 mm, and then trimethylsilylacetylene (3.83 mL, 27.3 mmol) is added. The mixture is stirred at rt for I h. The reaction is followed by LCMS (only 6% product after I h). The mixture is then transferred to a pressure tube and additional Pd(PPh3)2C12 (0.14 g, 0.199 mmol) and copper(l) iodide (0.036 g, 0.189 mmol) are added. The mixture is purged with N2 for 1 mm, and then it is heated at 60 C for 2 h (LCMS shows 54% mono-alkyne and 35% bis-alkyne). The reaction mixture is concentrated under reduced pressure. The residue is taken up in CH2CI2 and filtered through a plug of Celite. The Celite plug is washed with CH2CI2. The filtrate is washed with water (2x) and brine (lx), dried over Na2SO4, filtered and concentrated. The residue is chromatographed over silica gel (120 g ISCO column) eluting with 0-5% EtOAc/hexane gradient to yield a mixture of methyl 2-amino-5- bromo-3-((trimethylsilyl)ethynyl)benzoate and methyl 2-amino-3, 5- bis((trimethylsilyl)ethynyl)benzoate (4.2 to I ratio by I H NMR). LCMS (ES API) MH+ = 326 & 328 for Br isotopes mono-alkyne product; and LCMS (ES API) MH+ = 344 bis-alkyne product.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-5-bromo-3-iodobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BECHERER, J. David; CADILLA, Rodolfo; DEATON, David Norman; HAFFNER, Curt; HENKE, Brad Richard; PREUGSCHAT, Frank; SCHULTE, Christie; (69 pag.)WO2016/87975; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com