Tag: M.W=300-400

Electric Literature of 31827-94-8, 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. 31827-94-8, name is 2-Bromo-1-(4-iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows.

Step A18b. A solution of the compound from step A18a (512 mg, 1.86 mmol) in (( (5 mL) was treated with DIPEA (0.45 mL, 2.58 mmol) and MsCl (0.16 mL, 2.07 mmol) for 2 hours at 0 C before being partitioned (CH2Cl2-water). The organics were washed with brine, dried ( a2S04), filtered and evaporated to give the crude desired compound as a colorless oil (725 mg), which was used directly in the next step. ESIMS m/z = 254.20 [M-Boc+2H]+. Step A18c. A solution of the compound from step A18b (1.82 mmol at most) in DMF (5 mL) was treated with 15-crown-5 (80 mg, 0.36 mmol) and al (1.36 g, 9.1 mmol) in the presence of K2CO3 (1.12 g, 8.12 mmol) at 90 C overnight before being cooled down and partitioned (EtO Ac -water). The organics were washed with water, brine, dried ( a2S04), filtered and evaporated. The residue was purified by chromatography (silica, hexanes- ethyl acetate) to give the desired compound as a colorless oil (396 mg, 56%) containing an isomeric impurity. ESIMS m/z = 386.10 [M+H]+. Step A18d. A solution of the compound from step A18c (516 mg, 1.34 mmol) in toluene (10 mL) was treated with totally 4 portions of Bu4SnH (0.36 mL, 1.34 mmol) and AIBN (22 mg, 0.134 mmol) for 12 hours at 110 C before being cooled down and evaporated. The residue was purified by chromatography (silica, hexanes-ethyl acetate) to give the desired compound as a colorless oil (177 mg, 51%) as a single isomer. ESIMS m/z = 260.10 [M+H]+. Step A18e. A solution of the compound from step A18d (170 mg, 0.655 mmol) in CH2CI2 (3 mL) was treated with DAST (0.18 mL, 1.32 mmol) at 0 C for 1 hours before being quenched with aqueous aHC03 dropwisely and partitioned (CH2Cl2-water). The organics were washed with brine, dried ( a2S04), filtered and evaporated. The residue was purified by chromatography (silica, hexanes-ethyl acetate) to give the desired compound as a colorless oil (177 mg, 51%). ESIMS m/z =260.10 [M+H]+. Step A18f. The desired compound was prepared from the compound from step A18e using procedures similar to that described in Intermediate A7. ESIMS m/z = 472.11 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-(4-iodophenyl)ethanone. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; NOVARTIS AG; QIU, Yao-ling; CAO, Hui; PENG, Xiaowen; GAO, Xuri; OR, Yat, Sun; SWEENEY, Zachary, Kevin; WO2015/17382; (2015); A1;,
Iodide – Wikipedia,
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Some common heterocyclic compound, 51839-15-7, name is Dimethyl 5-iodoisophthalate, molecular formula is C10H9IO4, 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: 51839-15-7

General procedure: A 5 mL microwave glass vial (Biotage) sealable with a septum held in place by a metal crimp cap was charged with a diaryliodonium triflate (0.3 mmol, 1 equiv), an aryl iodide (1.5 mmol, 5 equiv.), and 1,2-dicholoroethane (3 mL, 0.1 M iodonium triflate concentration). The tube was sealed (crimp cap) and submitted to microwave irradiation with a target temperature of 100 C in high absorption mode. After the indicated time, the tube was retrieved and cooled to rt and the contents were concentrated under reduced pressure. The crude material was purified by silica gel flash chromatography (gradient 10 ? 50% acetone/CH2Cl2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51839-15-7, its application will become more common.

Reference:
Article; Racicot, Leanne; Ciufolini, Marco A.; Tetrahedron; vol. 73; 50; (2017); p. 7067 – 7072;,
Iodide – Wikipedia,
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148870-57-9, name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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. Recommanded Product: 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one

A mixture of the iodo-compound of formula (III) (50.00 g; 129 mmol), amine hydrochloride of formula (IV) (31.50 g; 129 mmol), potassium carbonate (37.70 g; 273 mmol), toluene (80 ml) and water (40 ml) was heated to 70C with stirring under an argon atmosphere. Reaction progress was monitored by HPLC. Upon completion, the reaction mixture was cooled to 23 C, diluted with toluene (105 ml), and filtered through a pad of celite. The filter cake was washed with additional toluene (60 ml). To the filtrate, water (50 ml) was added, and the mixture was shaken. The organic layer was separated and washed with additional water (80 ml). The separated organic layer was then extracted with 9% aqueous hydrochloric acid (507 g) in three portions. Yield of dehydroivabradine hydrochloride in combined acidic extracts was calculated based on HPLC assay using an external standard. The product was obtained in 80% yield as an aqueous solution which was used directly in the next step.

The synthetic route of 148870-57-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNTHON BV; MEL?A, Petr; ZABADAL, Miroslav; WO2014/114341; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 755027-18-0, 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. 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

1-Bromo-4-iodo-2-methoxybenzene (50 g, 160 mmol) was suspended in dichloromethane (75 mL) at -10 C. Boron tribromide (250 mL, 250 mmol, 1M in CH2Cl2,) was cannulated in over 30 minutes, with the internal temperature remaining below 0 C throughout the addition. After the addition, the mixture was stirred at 0 C for 1 h, and then at room temperature for 16 h. The mixture was cooled in an ice bath and 10% aqueous Na2CO3 (250 mL) was added in portions. The mixture was then partitioned between H2O and dichloromethane. The dichloromethane layer was dried over MgSO4 and then filtered.2-Bromo-5-iodophenol (46 g, 96%) was obtained from the filtrate as a pinkish-white solid. 1H NMR (acetone-d6) d: 9.24 (br s, 1H), 7.38 (d, J= 2 Hz, 1H), 7.31 (d, J= 8.5 Hz, 1H), 7.17 (dd, J= 8.5 Hz, 2 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-iodo-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PTC THERAPEUTICS, INC.; ZHANG, Nanjing; BABU, Suresh; BARRAZA, Scott J.; BHATTACHARYYA, Anuradha; CHEN, Guangming; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; SYDORENKO, Nadiya; TURPOFF, Anthony; WOLL, Matthew, G.; YAN, Wuming; (0 pag.)WO2020/5877; (2020); A1;,
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. 31827-94-8, name is 2-Bromo-1-(4-iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromo-1-(4-iodophenyl)ethanone

General procedure: The appropriate carbonyl compound (50 mmol) was dissolved in 50 mL of ethanol and magnetically stirred with an equimolar quantity of thiosemicarbazide for 24 h at room temperature with catalytic amounts of acetic acid. The desired thiosemicarbazone precipitated from reaction mixture, was filtered, crystallized from suitable solvent, and dried. Equimolar quantities of 4-iodo-acetophenone and bromine, both dissolved in chloroform, were stirred for 4 h at room temperature until the presence of HBr disappeared. The solution was evaporated under vacuum and the obtained pale yellow solid was washed with petroleum ether to give alpha-bromo-4-iodo-acetophenone in good yield (94%). Equimolar amounts of the prepared thiosemicarbazone (50 mmol) and alpha-bromo-4-iodo-acetophenone (50 mmol), both suspended in 50 mL of ethanol, were reacted at room temperature under magnetic stirring for 10 h. The precipitate was filtered and purified by chromatography to give compounds 1-25 in high yield.

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 31827-94-8.

Reference:
Article; Secci, Daniela; Bizzarri, Bruna; Bolasco, Adriana; Carradori, Simone; D’Ascenzio, Melissa; Rivanera, Daniela; Mari, Emanuela; Polletta, Lucia; Zicari, Alessandra; European Journal of Medicinal Chemistry; vol. 53; (2012); p. 246 – 253;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 25252-00-0 as follows. HPLC of Formula: C7H4BrIO2

Preparation of 4-bromo-3-hydroxymethyl-1-iodo-benzene Oxalyl chloride (13.0 mL) is added to an ice-cold solution of 2-bromo-5-iodo-benzoic acid (49.5 g) in CH2Cl2 (200 mL). DMF (0.2 mL) is added and the solution is stirred at room temperature for 6 h. Then, the solution is concentrated under reduced pressure and the residue is dissolved in THF (100 mL). The resulting solution is cooled in an ice-bath and LiBH4 (3.4 g) is added in portions. The cooling bath is removed and the mixture is stirred at room temperature for 1 h. The reaction mixture is diluted with THF and treated with 0.1 M hydrochloric acid. Then, the organic layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried (Na2SO4) and the solvent is evaporated under reduced pressure to give the crude product. Yield: 47.0 g (99% of theory)

According to the analysis of related databases, 25252-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM VETMEDICA GMBH; REICHE, Dania Birte; JOHNSTON, Laura; MOHREN, Nicole; US2014/303096; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 1022128-96-6, A common heterocyclic compound, 1022128-96-6, name is 2-Bromo-6-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

General procedure: A mixture of ortho-diiodobenzoic acid derivative (2.67 mmol,1.0 equiv.), NIS (2.0 equiv.), and 1,2-dichloroethane (DCE; 10 mL) were added to a flame-dried 100 mL round-bottom flask, and the mixture was irradiated with 100 W (tungsten lamp) under reflux conditions for 24 h. The reaction mixture was then cooled to room temperature. The mixture was then washed withsaturated NaHSO3, saturated NaHCO3, and brine. The organic layers were collected and then dried over anhydrous Na2SO4, filtered, and concentrated in a rotary evaporator. The residue was then purified by flash chromatography on silica gel (100% hexane) to give the desired iodinated product.

The synthetic route of 1022128-96-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Al-Zoubi, Raed M.; Al-Mughaid, Hussein; McDonald, Robert; Australian Journal of Chemistry; vol. 68; 6; (2015); p. 912 – 918;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 263351-43-5, name is tert-Butyl 3-iodobenzylcarbamate, 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. Application In Synthesis of tert-Butyl 3-iodobenzylcarbamate

tert-Butyl 3-iodobenzylcarbamate (0.67 mmol) was dissolved in 1 mL of dry DMF and the resultant solution was evacuated to 40 mm pressure and then released to N2 (g) three times. Triethylamine (1:8 ratio with DMF, 100 muL), Pd(PPh3)2Cl2 (0.030 mmol), and CuI (0.067 mmol) were added. The resultant mixture evacuated to 40 mm pressure for Ca. 30 seconds and then released to N2 (g). Finally, the alkyne 4 (0.67 mmol) in DMF (0.07 M) was added dropwise via an addition funnel over 40 minutes. The reaction mixture was stirred at room temperature for 18 hr and then diluted with ethyl acetate, poured into 0.1 M HCl and extracted with EtOAc (3¡Á100 mL). The combined organic layers were washed with water and brine and dried over MgSO4. The extract was concentrated and the product purified by Biotage chromatography (40M, product loaded onto SiO2) with 2% MeOH/CH2Cl2 to afford the desired title compound: 1H NMR (400 MHz, DMSO-d6) delta 8.24 (m, 1H), 7.50 (dd, J=4, 16 Hz, 1 H), 7.41 (m, 1H), 7.26 (m, 3H), 7.18 (m, 2H), 7.05 (m, 1H), 4.71 (m, 1H), 4.08 (m, 3H), 3.70 (dd, J=4, 12 Hz, 1H), 3.62 (m, 4H), 3.40 (m, 2H), 2.92 (m, 4H), 2.47 (m, 4H), 1.83 (s, 3H), 1.79 (m, 2H), 1.38 (s, 9H).

The synthetic route of tert-Butyl 3-iodobenzylcarbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Harris, Christina Renee; US2004/204463; (2004); A1;,
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. 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Methyl 5-bromo-2-iodobenzoate

To a stirred mixture of NaBH4 (11.18 g, 0.296 mol) in EtOH (200 ML) at 5 C. was added the product from Example 62A (50.4 g, 0.148 mol) in THF (100 ML).The mixture was alowed to warm to room temperature and stirred for 18 hours.The mixture was treated with additional NaBH4 (8.4 g, 0.222 mol) and was stirred for 22 hours.The mixture was cooled to 0 C., treated with 100 ML of 15% aqueous citric acid slowly, and extracted with 600 ML of CH2Cl2.The organic phase was washed with 200 ML of 15% NaCl and concentrated to provide the title compound. 1H NMR (CDCl3, 400 MHz) delta 7.64 (d, J=8 Hz, 1H), 7.61 (d, J=4 Hz, 1H), 7.12 (dd, J=4, 8 Hz, 1H), 4.63 (d, J=8 Hz, 2H), 1.98 (t, J=8 Hz, 1H). MS (DCl/NH3) [M+NH4]+ at 330, [M+NH4-H2O]+ at 312.

The synthetic route of 181765-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Altenbach, Robert J.; Black, Lawrence A.; Chang, Sou-Jen; Cowart, Marlon D.; Faghih, Ramin; Gfesser, Gregory A.; Ku, Yi-yin; Liu, Huaqing; Lukin, Kirill A.; Nersesian, Diana L.; Pu, Yu-ming; Sharma, Padam N.; Bennani, Youssef L.; US2004/92521; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 147808-02-4, name is 2-Fluoro-1,4-diiodobenzene, molecular formula is C6H3FI2, 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. Formula: C6H3FI2

Step 1-A: A solution of 2-fluoro-1,4-diiodo-benzene (804 mg, 2.31 mmol) in tetrahydrofuran (8 mL) was cooled to -78 C. (external) and a 2.0 M solution of isopropylmagnesium chloride in tetrahydrofuran (1.44 mL, 2.89 mmol) added via syringe. The resulting mixture was stirred for 30 minutes while allowing the temperature of the cooling bath to rise to -50 C. The reaction mixture was then immersed in an ice/water bath and anhydrous N,N-dimethylformamide (425 muL, 5.78 mmol) was added by syringe to the reaction mixture. The reaction was stirred at 0 C. for 10 minutes, then at room temperature for 5 minutes. Thin layer chromatography (TLC) indicated the reaction to be complete. The mixture was diluted with saturated aqueous ammonium chloride solution (8 mL) and extracted with diethylether (2*20 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by chromatography over silica gel gradient eluted with 0 to 15% v/v ethyl acetate/hexanes to give 2-fluoro-4-iodo-benzaldehyde as a fluffy-white solid (389 mg, 67%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 147808-02-4, its application will become more common.

Reference:
Patent; Chen, Shaoqing; Huby, Nicholas J.S.; Kong, Norman; Moliterni, Jonh Anthony; Morales, Omar Jose; US2009/170920; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com