Category: iodides-buliding-blocks

Reference of 148870-57-9, 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. 148870-57-9 name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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 6 3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-(methyl)amino]propyl}-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one Based on EP 0 534 859 A solution of the (d) camphorsulphonate salt obtained in Example 5 in ethyl acetate is brought to basic pH using sodium hydroxide and then the organic phase is separated off, washed, dried over Na2SO4 and evaporated. A mixture composed of 5.6 g of potassium carbonate, 2.2 g of the above amine in 100 mL of acetone and 4 g of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is then refluxed for 18 hours. The solvent is evaporated off in vacuo, and the residue is taken up in ethyl acetate and then extracted with 3N hydrochloric acid. The aqueous phase separated off is brought to basic pH using sodium hydroxide and is then extracted with ethyl acetate. After washing until neutral and drying over MgSO4, evaporation in vacuo is carried out to obtain 4.5 g of an oil which is purified on a silica column using a mixture of dichloromethane/methanol (90/10) as eluant. Yield=64%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Les Laboratoires Servier; Vaysse-Ludot, Lucile; Le Flohic, Alexandre; Vaultier, Michel; Pucheault, Mathieu; Kaminski, Thomas; US8859763; (2014); B1;,
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. 76801-93-9, name is 5-Amino-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide, A new synthetic method of this compound is introduced below., Computed Properties of C14H18I3N3O6

In a three-necked flask equipped with a stirrer and a reflux condenser,5-amino-N, N’-bis- (2,3-dihydroxypropyl) -2,4,6-triiodo-1,3-benzenedicarboxamide (84.6 g, 0.12 mol)N, N-dimethylacetamide (172 ml)Stir,Heated to 50 C dissolved, cooled to 10 C,A solution of chloroacetyl chloride (62 ml, 88.09 g, 0.78 mol)About 30min drop finished,The temperature was raised to 50 C for 3 h,Cooling to 0 ~ 10 ,At 10 ,Dropping 10 ml / L of sodium hydroxide solution 156 ml,Stir at room temperature for 1 h.After adding 100 ml of water, 59 ml of 1N hydrochloric acid was added dropwise, and the mixture was allowed to stand overnight. The filtrate was washed with water and dried to give 83.2 g of a yield of 90.0%.

The synthetic route of 76801-93-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiang Su Heng Rui Medicine Co., Ltd.; Hou, Xianshan; Wang, Junyan; Wang, Zhian; Zhong, Xinguang; (9 pag.)CN106278929; (2017); 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. 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, A new synthetic method of this compound is introduced below., name: 1,2-Dichloro-4-iodobenzene

(R)-2-(3,4-Dichloro-phenylamino)-propionic acid (62% ee) A mixture of 6.00 g (22.00 mmol) 3,4-dichloroiodobenzene, 2.94 g (33.00 mmol) D-alanine, 0.42 g (2.20 mmol) copper(I) iodide, 0.96 g (4.40 mmol) 2-hydroxybenzaldehyde phenylhydrazone, 14.00 g (66.00 mmol) tri-potassium phosphate in 32 ml of N,N- dimethylformamide was stirred at 80C for 16 h under argon, then after cooling diluted with water and acidified to pH 3 by addition of 25% aq. HC1 solution. The mixture was extracted with EtOAc (3x), the organic phases were washed with brine, dried (Na2S04), filtered and evaporated. Flash chromatography (Si02; dichloromethane/MeOH 95:5 to 4:1) afforded 3.11 g (60%)) of the title compound (as 81 :19 mixture of the (R) and (S) stereoisomers, BGB- 175*0.25 column) as light brown solid. MS: 231.9 (M-FT, 2C1).

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; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; BINGGELI, Alfred; GREEN, Luke; HARTMANN, Guido; MAERKI, Hans P.; MATTEI, Patrizio; WO2011/48032; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 41252-97-5, These common heterocyclic compound, 41252-97-5, name is 4-Iodo-2-nitrotoluene, 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 4-iodo-l-methyl-2-nitro-benzene (25.0 g, 107 mmol) in 300 mL of ethanol was added sulfided platinum (3.00 g) and ammonium formate (20.3 g, EPO 321 mmol). The mixture was heated to reflux for 12 h and then cooled to 22 C, filtered through Celite and concentrated in vacuo. The resulting residue was diluted with H2O (300 mL) and extracted with 3 x 200 mL CH2Cl2. The organic fractions were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to give b (21.1 g, 95%): MS m/z = 234 (M+H).

The synthetic route of 41252-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/41773; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 63262-06-6, 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. 63262-06-6, name is 1,4-Dibromo-2,5-diiodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 2-(tributylstannyl)thiophene (20.7 g, 55.3 mmol) and1,4-dibromo-2,5-diiodobenzene (13.5 g, 27.7 mmol) in dry DMF (100 mL) was addedPd(PPh3)2Cl2 (0.78 g, 1.12 mmol). The mixture was stirred for 40 h at 80 C. Aftercooling to room temperature, the reaction mixture was poured into water and thenextracted with toluene. The combined organic layers were washed with water and driedover anhydrous Na2SO4. After filtration and evaporation, the crude product wasrecrystallized from methanol to provide 8 as a white solid (yield = 10.3 g, 93%).

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, 1,4-Dibromo-2,5-diiodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Komiyama, Hideaki; Adachi, Chihaya; Yasuda, Takuma; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1459 – 1466;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 61272-76-2, name is 4-Fluoro-2-iodoaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Fluoro-2-iodoaniline

General procedure: A sealed tube (50 mL) was charged with 2-haloaniline 1a (2mmol), CS2 (10 mmol), Na2S (4mmol) and DMF (2 mL) at room temperature under an argon gas atmosphere and the tube was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically at 110 °C for 12 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, 2 mL HCl (3 mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by dichloromethane (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel colum chromatography (eluent: petroleum ether / ethyl acetate) give the corresponding pure product 2a.

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

Reference:
Article; Zhang, Tianmiao; Qin, Weijing; Zhu, Ning; Han, Limin; Wang, Liubo; Hong, Hailong; Synthetic Communications; vol. 47; 20; (2017); p. 1916 – 1925;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 105202-02-6, name is 2-Iodo-5-(trifluoromethyl)aniline, 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 105202-02-6, name: 2-Iodo-5-(trifluoromethyl)aniline

To a solution of compound 53 (620 mg, 2.16 mmol) in DMF (5 mL) was added phenylacetylene (331 mg, 356 muL, 3.24 mmol), PdCI2(PPh3)2 (76 mg, 0.108 mmol), Cul (25 mg, 0.131 mmol) and Et3N (656 mg, 903 muL, 6.48 mmol) at 23 C. The reaction mixture was stirred for 6 h at 23 C before it was quenched with a saturated solution of NH4CI (10 mL) and diluted with EtOAc (50 mL). The layers were separated, and the organic layer was extracted with H20 (3 x 10 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, hexanes:EtOAc 5: 1 ) to give compound 54 (518 mg, 92%) as pale yellow solid. (0472) [00362] 1 H NMR (400 MHz, CDCI3) delta = 7.56 (m, 2H), 7.47 (dd, J = 8.5, 0.8 Hz, 1 H), 7.42 – 7.38 (m, 3H), 6.98 – 6.96 (m, 2H), 4.48 (brs, 2H); 13C NMR (101 MHz, CDCI3) delta = 147.8, 132.5, 131 .6, 131 .5 (q, J = 32.2 Hz), 128.7, 128.5, 124.0 (q, J = 272.3 Hz), 122.6, 1 14.3 (q, J = 3.8 Hz), 1 1 1 .2, 1 10.7 (q, J = 4.0 Hz), 96.5, 84.6; 19F NMR (376 MHz, CDCI3) delta = -63.13. m/z (ESI) 262.1 [M+H+].

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; THE GOVERNING COUNCIL OF THE UNIVERSITY OF TORONTO; GREIG, Iain; ZANDA, Matteo; TSENG, Chih-Chung; ROSS, Ruth; (134 pag.)WO2016/29310; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 774608-49-0, A common heterocyclic compound, 774608-49-0, name is 4-Bromo-1-chloro-2-iodobenzene, molecular formula is C6H3BrClI, 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.

j00340j To a solution of 4-bromo-1-chloro-2-iodobenzene (0.30 g, 0.95 mmol), cyclopropylboronic acid (97 mg, 1.1 mmol), [1,1 ?-bis(diphenylphosphino)ferrocenej dichloropalladium(II) (39 mg, 0.047 mmol) in dioxane (6 mL) and water (2 mL) under nitrogen at room temperature was added potassium phosphate (0.76 g, 3.6 mmol). The reaction mixture was stirred at 70 C for 3 hours, then diluted with water (10 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine (2 xlO mL), dried over sodium sulfate, filtered and concentrated in vacuo to give compound B-34 (0.30 g, crude) as a yellow oil.

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; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 387-48-4,Some common heterocyclic compound, 387-48-4, name is 3-Fluoro-2-iodobenzoic acid, molecular formula is C7H4FIO2, 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 mixture of 3-fluoro-2-iodobenzoic acid (1 .4 g, 5.26 mmol), 1 H-pyrazole (0.72 g, 10.5 mmol), trans-N, N’-dimethyl-cyclohexane-1 ,2-diamine (0.17 mL, 1 .05 mmol), Cul (50.1 mg, 0.26 mmol), dioxane (50 mL) and water (0.028 mL) was added CS2CO3 (3.43 g, 10.5 mmol). The reaction mixture was heated to 100 C for 1 h. The reaction mixture was cooled to ambient temperature then diluted with water. The aqueous layer was acidified to pH2 and extracted with EtOAc (30 mL) three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated. Purification (FCC), (DCM to 10%MeOH/1 %HOAC/DCM) afforded the title compound as a colorless oil (790 mg, 72%). 1H NMR (400 MHz, CDCI3): 7.85 – 7.73 (m, 1 H), 7.54 – 7.44 (m, 1 H), 7.44 – 7.34 (m, 1 H), 6.55 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Fluoro-2-iodobenzoic acid, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 61272-76-2, A common heterocyclic compound, 61272-76-2, name is 4-Fluoro-2-iodoaniline, molecular formula is C6H5FIN, 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.

Example 55 4-(((5-Fluoro-2-(triethylsilyl)-1H-indol-3-yl)methoxy)methyl)-N,N-dimethyl-1-(thiophen-2-yl)cyclohexanamine (one of two possible diastereomers) A degassed mixture of Ain-09 (795 mg, 2 mmol), 4-fluoro-2-iodoaniline (567 mg, 2.4 mmol), [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II) chloride (PEPPSI, 273 mg, 0.4 mmol) and sodium carbonate (1.06 g, 10 mmol) in anhydrous and oxygen-free N,N-dimethyl formamide (10 ml) was stirred for 18 h at 100° C. The solvent was then removed under vacuum and the residue divided between water and diethyl ether (20 ml each). The phases were separated and the aqueous phase was extracted with diethyl ether (3*10 ml). The combined organic phases were washed with water and 1 M sodium thiosulfate solution (20 ml each), dried with sodium sulfate and concentrated to small volume under vacuum. The crude product (1.30 g) was purified by flash chromatography (100 g, 20*4.0 cm) with ethyl acetate/cyclohexane (1:9). Yield: 552 mg (55percent), brownish oil 1H-NMR (DMSO-d6): 0.82-0.98 (m, 15H); 1.30-1.70 (m, 7H); 1.96 (s, 6H); 2.37 (br d, 2H); 3.25-3.33 (m, 2H); 4.58 (s, 2H); 6.88-7.04 (m, 3H); 7.23-7.31 (m, 1H); 7.35-7.41 (m, 2H); 10.77 (s, 1H). 13C-NMR (DMSO-d6): 3.1; 7.2; 24.4; 34.6; 37.1; 37.4; 58.2; 64.4; 74.7; 102.8 (d, J=23 Hz); 109.6 (d, J=27 Hz); 112.1 (d, J=10 Hz); 121.5; 123.0; 123.8; 126.0; 128.7 (d, J=10 Hz); 135.3; 135.9; 145.0; 156.7 (d, J=231 Hz).

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