Tag: M.W=200-300

13526-66-4, Adding a certain compound to certain chemical reactions, such as: 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, belongs to chlorides-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 13526-66-4.

[00359] EX. 8-29 free base and hydrochloride salt were prepared in 50 g scale according the following procedures. D [00360] To a solution of 3-bromo-6-chloroinnidazo[1 ,2-b]pyridazine (150 g, 0.65 mol) and 3-(trifluoromethyl)phenylboronic(143 g, 0.65 mol) in dioxane/H2O(2.5 L: 4:1 ) was added K2CO3 (180 g, 1 .3 mol) and Pd(PPh3)4 (10 g, 10 mmol). The mixture was stirred at 80 C for 24 h. The solution was concentrated, partitioned with EA/H2O. The aqueous layer was extracted with EA (500ml_) for 3 times. The collected organic layers was dried over Na2SO , concentrated and purified by column chromatograph (PE:EA, 3:1 to 2:1 ) to give 6-chloro-3-(3-(trifluoromethyl)phenyl)imidazo[1 ,2-b]pyridazine (135.15 g, 70.3%) as yellow solid.

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, 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOLERO PHARMACEUTICALS, INC.; XU, Yong; BRENNING, Benjamin, Gary; KULTGEN, Steven, G.; LIU, Xiaohui; SAUNDERS, Michael; HO, Koc-Kan; WO2013/13188; (2013); A1;,
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A common heterocyclic compound, 98577-44-7, name is 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane, molecular formula is C5H6Br2Cl2, 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. 98577-44-7.

Tricyclo [1.1.1.01’3] pentane Methyllithium (46.3 mL, 74.1 mmol, 1.6M in diethyl ether) was added to a solution of l,l-dibromo-2,2-bis(chloromethyl)cyclopropane (10 g, 33.7 mmol) in pentane (10 mL) stirred at -78C for 15 min. After the reaction mixture was maintained at -78C for 15 min, the reaction flask was removed from the dry ice/acetone bath and placed in an ice-water bath. The reaction mixture was stirred at that temperature for 2 hrs. The volatiles, which was warmed at 40C by using an oil bath, were collected via a shortpath distillation condenser under a dry-ice-acetone environment. The condensed material was used in next reaction without further purification.

The synthetic route of 1,1-Dibromo-2,2-bis(chloromethyl)cyclopropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; EASTMAN, Kyle J.; PARCELLA, Kyle E.; WO2014/159559; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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. 13526-66-4

Example 70(?)-2-(1-(3-((1 -Methyl-1 H-indazol-5-yl)methyl)imidazo[1 ,2-b]pyridazin-6-yl)ethylidene) hydrazinecarboxamide(6-Chloroimidazo[1 ,2-b]pyridazin-3-yl)(1 -methyl-1 H-indazol-5-yl)methanol (70.1)To a solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (232.0 mg, 1.00 mmol) in 5 ml_ THF, was added ethylmagnesium bromide (1.50 ml_, 1.50 mmol) at -10 0C. After stirring at – 10 0C for 1 hour, 1 -methyl-1 H-indazole-5-carbaldehyde (240.0 mg, 1.50 mmol) was added. The mixture was allowed to warm to room temperature slowly and stirred for additional 2 hours. The reaction was quenched with Sat. NH4CI solution and concentrated under reduced pressure. The residue was diluted with water, and extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4 and concentrated. The crude product was washed with DCM to give the title compound as a white solid (230 mg, 70 %). 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.21 (d, 1 H), 8.02 (s, 1 H), 7.81 (s, 1 H), 7.59 (d, 1 H), 7.56 (s, 1 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 6.29 (d, 1 H), 6.21 (d, 1 H), 4.02 (s, 3H). LCMS (method A): [MH]+ = 314, tR = 4.44 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13526-66-4, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Xingnian; HE, Feng; LI, Yue; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YU, Zhengtian; ZHANG, Ji Yue (Jeff); DAI, Miao; WO2011/18454; (2011); A1;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 24279-39-8, name is 2,6-Dichloro-4-(trifluoromethyl)aniline, belongs to chlorides-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 24279-39-8, 24279-39-8

REFERENCE EXAMPLE 3 Nitrosyl sulphuric acid, prepared from sodium nitrite (69 g, 1 mol) and concentrated sulphuric acid (600 ml) was added dropwise with stirring to a cooled solution of 2,6-dichloro-4-trifluoromethylaniline (230 g, 1 mol) in glacial acetic acid (1250 ml) at 15-20 C. The mixture was stirred for 1 hour at ambient temperature. The diazonium mixture was run slowly into a solution prepared from cuprous bromide (143.4 g, 1 mol), hydrobromic acid (48%, 1 l) and ice (approx. 1000 g) at a rate so as not to exceed a temperature of 35 C. After 1 hour the mixture was steam distilled to give 1 l of distillate which was diluted with water (3 l) and extracted with diethyl ether (2*500 ml). The organic fractions were combined and washed with aqueous sodium hydroxide solution (2M, 2*250 ml) and water (250 ml), dried over anhydrous sodium sulphate and evaporated to dryness. The oily residue was distilled to give 1-bromo-2,6-dichloro-4-trifluoromethylbenzene (256.8 g) as a colourless liquid, b.p. 74-78 C. at 6 mmHg.

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, 2,6-Dichloro-4-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; May & Baker Limited; US5206257; (1993); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13918-92-8, Name is 2,4-Difluorobenzene-1-sulfonyl chloride, 13918-92-8, belongs to chlorides-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.

Step EN-(5-bromo-2-meth enzene- sulfonamide[00299] 2,4-difluorobenzene-1-sulfonyl chloride (6.8 g, 32 mmol) was added into a solution of 5-bromo-2-methoxypyridin-3-amine (6.5 g, 32 mmol) in pyridine (10 mL) and the reaction mixture was stirred at r.t. for 20 hours before the reaction solution was concentrated to dry in vacuo to give a crude product which was purified with column chromatography (EtOAc : Petroleum ether = 1 :2 as eluent) to give the product as a brown solid (10 g, 83%). 1 H-NMR (300 MHz, DMSO-d6), delta 10.46 (s, 1 H), 8.52 (s, 1 H), 7.80-7.72 (m, 2H), 7.56 (m, 1 H), 7.20 (m, 1 H), 3.62 (s, 3H). LC/MS, ESI, m/z, 379, 381 (m+1 )+, Br pattern found.

Statistics shows that 2,4-Difluorobenzene-1-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 13918-92-8.

Reference:
Patent; GLAXOSMITHKLINE LLC; BOTYANSZKI, Janos; DICKERSON, Scott Howard; LEIVERS, Martin Robert; LI, Xiaofei; MCFADYEN, Robert Blount; REDMAN, Aniko Maria; SHOTWELL, John Bradford; XUE, Jianjun; WO2012/174312; (2012); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 64628-73-5, name is 3-Chloro-4-(trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life. 64628-73-5

General procedure: A dry, 50 mL round bottom flask was charged with a magnetic stir bar then sealed with a septum and flushed with nitrogen. To this was added the salicylic acid derivative (2.0 mmol) and dichloromethane (10 mL). While stirring, SOCl2 (10 mmol) was added dropwise, followed by dimethylformamide (0.05 mmol), and the mixture was allowed to stir at room temperature under nitrogen for 12 hours. At this point, the mixture was concentrated under vacuum to afford the solid acid chloride derivative which was used immediately without further purification. The flask containing the acid chloride was then re-sealed with a septum and placed under a nitrogen atmosphere, and its contents were re-suspended in fresh dichloromethane (20 mL). While stirring, the aniline derivative (4.0 mmol) was added and the resulting opaque mixture was stirred for an additional 18 h. At this point, the mixture was quenched with ice water (5 mL) and phases were separated using a separatory funnel. The aqueous layer was extracted twice with dichloromethane (20 mL) then the organic layers were combined and washed with brine (40 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated under vacuum to afford a crude solid residue. This residue was then re-suspended in dichloromethane (10 mL) and adsorbed onto silica gel (1 g), then chromatographed on a 12 g silica gel column using a solvent gradient of 0-40% ethyl acetate in hexanes over 25 min. The product-containing fractions were combined then concentrated under vacuum to afford the purified salicylamide derivative.

The chemical industry reduces the impact on the environment during synthesis 64628-73-5. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chae, Hee-Don; Cox, Nick; Capolicchio, Samanta; Lee, Jae Wook; Horikoshi; Kam, Sharon; Ng, Andrew A.; Edwards, Jeffrey; Butler, Tae-Leon; Chan, Justin; Lee, Yvonne; Potter, Garrett; Capece, Mark C.; Liu, Corey W.; Wakatsuki, Soichi; Smith, Mark; Sakamoto, Kathleen M.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 16; (2019); p. 2307 – 2315;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

202197-26-0, A common heterocyclic compound, 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, molecular formula is C13H11ClFNO, 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 100-ml three-necked round bottom flask was charged with 15 ml of water, At 0 deg C (0.45 g, 1.81 mmol) 3-chloro-4- (3-fluorobenzyloxy)aniline and NaNO2 (0.25 g, 3.62 mmol) were successively added with stirring, HCl (0.19 g, 5.42 mmol) was added dropwise, Speed can not be too fast, After completion of the dropwise addition, The temperature of the reaction system was maintained at 0-5 deg C for 1.5 h. The color of the reaction liquid was deepened. An aqueous solution of NaN3 (0.14 g, 2.17 mmol) was then added, Must be added and the speed can not be too fast, During the addition, a large amount of foam is generated, Reaction solvent water is added at this time. After completion of the addition, the reaction was continued for 3 h while the temperature was kept constant, and the progress of the reaction was monitored by TLC during the reaction. During the course of the reaction, the color of the reaction solution was found to change from dark yellow to light yellow with yellow foam. At the end of the reaction, The reaction solution was extracted with EA (3 * 40 ml)The organic phase was washed with brine (3 * 10 ml) The organic phases were combined, Mg2SO4 concentrate, Purification by silica gel column chromatography gave 0.48 g (yield: 95.05%) of a yellow solid.

The synthetic route of 202197-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin International Joint Academy of Biotechnology & Medicine; Chen, Yue; Rao, Zihe; Yang, Cheng; Bai, Cuigai; Zhang, Wei; Pan, Chengwen; Meng, Fanfei; Wang, Song; (11 pag.)CN103159748; (2016); B;,
Chloride – Wikipedia,
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13745-86-3, Name is 11-Chlorodibenzo[b,f][1,4]thiazepine, 13745-86-3, belongs to chlorides-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.

21.6 g of 11-chloro-dibenzo [b, f] [l, 4] thiazepine was dissolved in 120 ml of xylene, stirred and 5.0 gPiperazine, 1.2 g of potassium iodide and 24 g of potassium carbonate were added and the reaction temperature was controlled to 105 to 115 C and kept at the same temperature for 5 hours. Insulation finishedBi to 20 ~ 30 C, add 100ml of purified water washing and stirring for 20 minutes, and then suction filtration. The filtered solid was re-added100ml purified water was beaten and the obtained product was filtered and purified. The purity was 99.5% and the yield was 88.0%.

Statistics shows that 11-Chlorodibenzo[b,f][1,4]thiazepine is playing an increasingly important role. we look forward to future research findings about 13745-86-3.

Reference:
Patent; Qilu Tianhe Pharmaceutical Co., Ltd.; Zhang, Wenwen; Guan, Qinghua; Zhang, Xiaoyong; Fan, Changying; Li, Baoyong; Wu, Ke; Zhang, Zhaozhen; Dong, Tinghua; Du, Yunfeng; (5 pag.)CN104447616; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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. 33863-76-2.

EXAMPLE 8.0 8-(1-(3-chloro-5-fluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (single enantiomer) To a mixture of 8-(1-aminoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (350 mg, 1.01 mmol, single enantiomer, [alpha]D20: +35 in acetonitrile), cesium carbonate (1288 mg, 3.95 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (147 mg, 0.25 mmol) and 1-bromo-3-chloro-5-fluorobenzene (467 mg, 2.23 mmol) in degassed 1,4-dioxane (2 ml), was added tris(dibenzylideneacetone)dipalladium (70 mg, 0.08 mmol). The suspension was heated in a sealed container at 95 C. for 16 hrs. The reaction mixture was filtered through a short pad of dicalite and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with 0 to 8% isopropanol in DCM. The solvent was evaporated to dryness, the product triturated with diethyl ether-DCM (9:1), collected by filtration and dried to afford 8-(1-(3-chloro-5-fluorophenylamino)ethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (320 mg; 67%) as a clear yellow solid. Mass Spectrum: M+H+ 474. [alpha]D20: -138. NMR Spectrum (DMSOd6): 1.52 (d, 3H), 2.75 (bs, 3H), 2.95 (bs, 3H), 3.49-3.63 (m, 4H), 3.70-3.79 (m, 4H), 4.98-5.07 (m, 1H), 5.60 (s, 1H), 6.23 (d, 1H), 6.42 (d, 1H), 6.43 (ddd, 1H), 6.94 (d, 1H), 7.54 (d, 1H), 7.80 (d, 1H).

The synthetic route of 1-Bromo-3-chloro-5-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2011/98271; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, belongs to chlorides-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. 933190-51-3

A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (300 mg, 1.3 mmol), (S)-6-(2-methylpyrrolidin-1-yl)pyridin-2-amine (252 mg, 1.42 mmol), Pd2(dba)3 (75 mg, 0.13 mmol), BINAP (324 mg, 0.52 mmol), Cs2CO3 (1272 mg, 3.9 mmol) and dioxane (20 mL) was heated to 100 C. with stirring for 16 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200-300 mesh, petroleum ether:ethyl acetate=3:1) to give (S)-6-chloro-N-(6-(2-methylpyrrolidin-1-yl)pyridin-2-yl)imidazo[1,2-b]pyridazin-8-amine (124 mg, 29%) as a yellow solid. LC-MS: [M+H]+, 329.0, tR=1.951 min.

Statistics shows that 933190-51-3 is playing an increasingly important role. we look forward to future research findings about 8-Bromo-6-chloroimidazo[1,2-b]pyridazine.

Reference:
Patent; Hoffmann-La Roche Inc.; Hermann, Johannes Cornelius; Kuglstatter, Andreas; Lucas, Matthew C.; Padilla, Fernando; Wanner, Jutta; Zhang, Xiaohu; US2013/109661; (2013); A1;,
Chloride – Wikipedia,
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