Month: May 2021

Electric Literature of 180624-08-2, 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. 180624-08-2, name is 4-Bromo-2-iodo-6-nitroaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-Bromo-5-iodonitrobenzene.4-bromo-2-iodo-6-nitroaniline (5 g, 0.0145 mol) was added in portions to stirred concentrated sulfuric acid (60 ml) keeping the temperature at 0-50C. After stirring in the cold for 1 h, sodium nitrite (2.3 g, 0.0326 mol) was added and the reaction mixture stirred in the cold for a further 2 h. The reaction mixture was then poured into ice (250 ml). The resultant mixture was added, in portions, to a boiling solution of copper (II) sulfate (0.36 g, 0.00145 mol) in ethanol (150 ml) and boiled for a further 2 h. The reaction mixture was cooled to ambient temperature and extracted with ethyl acetate (300 ml) which was washed with saturated sodium hydrogen carbonate solution (250 ml) and dried (MgSO4). The solvent was removed in vacuo to give 3- Bromo-5-iodonitrobenzene as a yellow solid (4.21 g, 88 %) which was used without further purification. 1H NMR (400MHz,delta,CDCI3): 8.18(1 H,s), 8.34(1 H,s), 8.50(1 H,s)

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, 4-Bromo-2-iodo-6-nitroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROLYSIS LTD.; WO2007/148093; (2007); 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. 59382-39-7, name is 1-Fluoro-4-iodo-2-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., name: 1-Fluoro-4-iodo-2-(trifluoromethyl)benzene

Sequentially add 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (300 mg, 2. 2 mmol), (bis (triphenylphosphine) palladium (II) dichloride (69 mg, 0. 10 mmol), and copper (I) iodide (38 mg, 0. 198 mmol) to a solution of 1-fluoro-4-iodo-2-trifluoromethylbenzene (575 mg, 1. 98 mmol) in triethylamine (4 mL) under nitrogen. Heat at 70 C for 2. 5 h and concentrate. Purify the residue by silica gel chromatography, eluting from 0 : 100 to 20 : 80 using ethyl acetate : hexanes, to give the title compound as a white solid (520 mg, 88%). 1HNMR (300 MHz, CDCl3) 8 7. 19-7. 23 (m, 1H), 7. 67-7. 74 (m, 1H), 7. 79-7. 87 (m, 2H), 8. 55 (d, J = 2. 3 Hz, 1H), 8. 63 (d, J = 1. 7 Hz, 1H) ; MS (APCI) m/z= 300 [M+H] +.

The synthetic route of 59382-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 7212-28-4, name is 2-Iodo-N-phenylacetamide, 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. category: iodides-buliding-blocks

EXAMPLE 146 Trans-2-carboxy-5,7-dichloro-4-(phenylaminocarbonylmethylamino)-1,2,3,4 -tetrahydroquinoline hydrochloride This material was prepared by the method given in Example 145 step a and b) using phenylaminocarbonylmethyliodide in place of benzyl bromide to yield the title compound as colourless crystals, m.p. 163-164.2 C. dec.; delta (360 MHz, DMSO) 1.93 (1H, ddd, J=13.3, 12.2 and 3.8 Hz, CHA CHB HC CHD), 2.73 (1H, dm, J=13.3 Hz, CHA CHB HC CHD), 4.00 (2H, 2d, J=16.2 Hz, NHCH2 CONHPh), 4.32 (1H, dd, J=12.2 and 3.8 Hz, CHA CHB HC CHD), 4.78 (1H, bs, CHA CHB HC CHD), 6.73 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.92 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.10 (1H, m, ArH), 7.18 (1H, s, ArNH), 7.35 (2H, m, 2 ArH), 7.60 (2H, m, 2 ArH), 9.5 (2H, bm, NH2), 10.72 (1H, m, CHD NHCH2). m/e (FAB+) 394 (M+1). Found C, 46.73; H, 4.28; N, 8.75; C18 H17 Cl2 N3 O3.1.9HCl requires C, 46.50; H, 4.32; N, 9.05%.

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

Reference:
Patent; Merck Sharp & Dohme, Ltd.; US5231102; (1993); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 132131-24-9, name is 2-Amino-5-iodobenzonitrile, 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 132131-24-9, Recommanded Product: 132131-24-9

(ii) Preparation of N’-(2-cyano-4-iodo-phenyl)-N,N-dimethyIformamidine (8): Into a 500 ml 3 necked round bottomed flask, N, N-dimethylforamide (100 ml), 2- amino-5-iodobenzonitrile (50g) obtained by the process given in the above step (i) and Nu,Nu-dimethyl formamide dimethyl acetate (51.3 g) were charged. The reaction mass was maintained at 70-75 C for about 2 Hrs. The completion of the reaction was monitored by TLC. The reaction mass was cooled to 25-35 C and quenched into ice water and maintained for about 2 Hrs. at 0-5 C. The product was filtered and dried under vacuum at 25-35 C to get 58 g of N’-(2-cyano-4-iodo-phenyl)-N,N- dimethylforrnamidine as a pale yellow coloured amorphous powder. Melting range: 53-55 CHPLC purity: 99.8%

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

Reference:
Patent; NATCO PHARMA LIMITED; JYOTHI PRASAD, Ramanadham; ADIBHATLA KALI SATYA, Bhujanga rao; VENKAIAH CHOWDARY, Nannapaneni; WO2011/39759; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5469-33-0, name is (Iodomethyl)cyclohexane, 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 (Iodomethyl)cyclohexane

[0344] To a solution of ethyl 8-CHLORO-6-HYDROXY-2- (TRIFLUOROMETHYL)-2H-CHROMENE-3- carboxylate prepared as in Example 17a, Step 3 (1.00 g, 3.10 mmole) in anhydrous DMF (10.0 mL) was added KI (51.5 mg, (0.310 mmole), K2CO3 (1.29 g, 9.30 mmole) and cyclohexyl iodide (1.20 mL, 9.30 mmole). The suspension was heated at 50 C for 17 h and then the temperature was slowly raised to 80 C and stirred overnight. Additional cyclohexyl iodide (1.20 mL, 9.30 mmole) was added and the temperature was maintained at 100-120 C for 3 days. The mixture was then cooled and poured into H20 (200 mL), which was saturated with solid NaCl. Following extraction with EtOAc (2 X 100 mL), the combined extracts were washed with brine (3 X 100 mL) and concentrated in vacuo. Purification by silica chromatography (6: 1 hexanes: EtOAc) gave 45 mg (3.5% yield) of the product: EIHRMS M/Z 404.0999 (M+, CL9H2OCIF304, Calc’d 404.1002).

The synthetic route of 5469-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 869365-97-9, These common heterocyclic compound, 869365-97-9, name is (5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone, 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.

(5-chloro-2-iodophenyl)(2-fluoro-6-methoxyphenyl)methanone (3)[0148] Into a reactor at room temperature was added 2 (67.6kg, 179mol) and MTBE (344L). The mixture was warmed to 40 C and stirred for 30rnin until solids fully dissolved. The mixture was then cooled to 25 to 30 C. Sodium methoxide as a 25% w/w solution in methanol (45.2kg, 209mol) was added over a minimum of 90min at 25 to 30 C. The reaction mixture was stirred for at least 2h until >99.0% conversion was obtained by HPLC analysis. Water (483L) was added slowly over 30min while maintaining the temperature between 20 and 25 C. The layers were separated and the aqueous phase was extracted with MTBE (77L). The combined organic extracts were washed with a dilute brine solution (38kg NaCl in 342L water). The organic layer was filtered, washed with water (242L) and the organic phase was filtered. The resulting organic phase was concentrated until 360L of solvent were removed while maintaining the internal temperature below 70 C. Isobutanol (302L) was added and the mixture was concentrated while maintaining the internal temperature below 70 C until 307L of solvent were removed. A second portion of isobutanol (330L) was added and the mixture was concentrated while maintaining the internal temperature below 70 C until 210L of solvent were removed. The mixture was heated to 60 to 85 C until a clear solution was obtained and cooled to 50 C. A slurry of seed crystals (50g in 150mL isobutanol) was added and the mixture was cooled to 40 C. A second slurry of seed crystals (30g in 60mL isobutanol) was added and the mixture was cooled to 20 to 25 C over a minimum of 3h. The resulting mixture was stirred an additional 2h. The mixture was filtered and washed with isobutanol (2 x 65L). The resulting wet cake was dried at 20 to 35 C under vacuum to provide 50.9kg of crude 3. Into a separate reactor was charged crude 3 and isobutanol (69L). The mixture was heated to 75 to 80 C until a clear solution was obtained. The reaction mixture was cooled to 55 C and a slurry of seed crystals (50g in 500mL isobutanol) was added. The mixture was stirred for 30rnin at 55 C, cooled to 20 to 25 C over a minimum of 3h and stirred an additional 2h. The mixture was filtered and washed with isobutanol (2 x 31L). The wet cake was dried under vacuum at 40 C to provide 46.0kg (66% yield) of purified 3. ? NMR (300 MHz, CDCL) delta 7.88 (d, J=8.2 Hz, 1H), 7.42 (m, 2H), 7.13 (dd, J=2.3, 8.2 Hz), 6.76 (m, 2H), 3.73 (s, 3H); MS (ESI) m/z 391.2 (M + H+, 30%).

Statistics shows that (5-Chloro-2-iodophenyl)(2,6-difluorophenyl)methanone is playing an increasingly important role. we look forward to future research findings about 869365-97-9.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; ARMITAGE, Ian; COOPER, Martin, I.; EDDLESTON, Mark, D.; FAIBER, Neil, C.; MCCUBBIN, Quentin, J.; WATT, Stephen, W.; WO2011/103089; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 4044-58-0, These common heterocyclic compound, 4044-58-0, name is 1-Bromo-8-iodonaphthalene, 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.

A mixture of Cul (1.57 g, 8.26 mmol, 1.1 eq) and KF (479 mg, 8.26 mmol, 193 pL, 1.1 eq) was thoroughly mixed and heated to 150 C under vacuum by using oil pump with heat gun with gentle shaking until an homogemeous greenish color was obtained. To the mixture was added DMSO (50 mL), trimethyl(trifluoromethyl)silane (3.20 g, 22.5 mmol, 3.0 eq) and l-bromo-8-iodo-naphthalene (2.5 g, 7.51 mmol, 1.0 eq) was added and the slurry was heated to 25 C for 16 h. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (3 c 30 mL). The combined organic layers were washed with brine (20 mL), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (column: Phenomenex Synergi C18 150*25* lOpm; mobile phase: [water (0.225% FA) – ACN]; B%: 66%- 86%, lOmin). l-bromo-8- (trifluoromethyl)naphthalene (900 mg, 3.14 mmol, 42% yield, 96% purity) was obtained as a white solid. (0758) [0436] *H NMR (400MHz, chloroform-d) d = 8.12 (d, J= 7.6 Hz, 1H), 8.10 – 8.02 (m, 2H), 7.90 (dd, J = 1.2, 8.0 Hz, 1H), 7.54 (t, J= 7.6 Hz, 1H), 7.37 (t, .7= 7.6 Hz, 1H).

Statistics shows that 1-Bromo-8-iodonaphthalene is playing an increasingly important role. we look forward to future research findings about 4044-58-0.

Reference:
Patent; MIRATI THERAPEUTICS, INC.; ARRAY BIOPHARMA, INC.; MARX, Matthew, Arnold; BLAKE, James, F.; FELL, Jay, Bradford; FISCHER, John, P.; MEJIA, Macedonio, J.; (164 pag.)WO2020/47192; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 615-43-0, The chemical industry reduces the impact on the environment during synthesis 615-43-0, name is 2-Iodoaniline, I believe this compound will play a more active role in future production and life.

Acetyl chloride (6 mmol) was added dropwise to the mixture of 2-iodoaniline (5 mmol) and sodium hydroxide (13 mmol) in THF/H2O (1/1, 4 mL). Stirred the mixture at 0 C. for 2 h, and then at room temperature for overnight. The mixture was diluted with 10 mL water and extracted with diethyl ether 3 times. The combined organic layer was washed with water 3 times and brine. Dried over sodium sulfate, filtered, and removed solvent. The residue was then purified by column chromatography afforded white solid of 2-iodoacetanilide 68% yield. NMR

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, 2-Iodoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; University of Massachusetts; US7473786; (2009); B1;,
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. 1252046-13-1, name is 2-Bromo-5-iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromo-5-iodobenzonitrile

Under an argon atmosphere, to a 500 ml, three-neck flask, 5.00 g of (6-bromopyridin-3-yl)boronic acid, 7.63 g of 2-bromo-5-iodobenzonitrile, 0.28 g of Pd(OAc)2, 1.02 g of SPhos, and 10.52 g of K3PO4 were dissolved in 120 ml of a deaerated mixture solvent of toluene/ethanol/water (10:1:2), followed by stirring at about 80 C. for about 12 hours. After finishing the reaction, water was added, and extraction with CH2Cl2 was conducted. An organic layer was separated and dried with MgSO4, and solvents were removed by distillation under a reduced pressure. The crude product thus obtained was separated by silica gel column chromatography to obtain 6.20 g (yield 74%) of Intermediate O. The molecular weight of Intermediate O measured by FAB-MS was 338.

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 1252046-13-1.

Reference:
Patent; Samsung Display Co., Ltd.; SAKAMOTO, Naoya; (128 pag.)US2019/296247; (2019); 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. 249647-25-4, name is 3-Bromo-4-iodobenzoic acid, A new synthetic method of this compound is introduced below., name: 3-Bromo-4-iodobenzoic acid

STEP 1 : 3-BROMO-4-IODO-N-(METHYLSULFONYL)BENZAMIDE (INTERMEDIATE D)[00338] A suspension of l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.586 g, 3.06 mmol), 4-(dimethylamino) pyridine (0.561 g, 4.59 mmol), methanesulfonamide (0.128 ml, 1.835 mmol) and 3-bromo-4-iodobenzoic acid (0.5 g, 1.529 mmol, HDH Pharma) was shaken at ambient temperature for 16 h. The reaction mixture was purified by reverse phase HPLC using water and acetonitrile and TFA as modifier to obtain Intermediate D (0.268 g, 0.663 mmol, 43.4 % yield) as a white sticky, solid. MS (ESI, positive ion) m/z 405.0.

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; AMGEN INC.; BREGMAN, Howard; CHAKKA, Nagasree; DIMAURO, Erin F.; GAO, Hua; GUNAYDIN, Hakan; HUANG, Hongbing; OLIVIERI, Philip; SCHENKEL, Laurie; WEISS, Matthew; WO2015/51043; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com