Tag: M.W=200-300

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 1127-85-1 as follows. 1127-85-1

Reference Example 36 (S)-tert-butyl 1-(2-chloro-5,6,7,8-tetrahydroquinazolin-4-yl)pyrrolidin-3-yl-(methyl)carbamate Diisopropylethylamine (2.7 ml, 15.5 mmol) was added into chloroform (40 ml) solution of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (1.5 g, 7.39 mmol) prepared in Reference Example 33 and (3S)-(-)-3-(methylamino)-pyrrolidine (0.87 ml, 8.13 mmol), and then they were stirred at 50 C. overnight. Di-tert-butyldicarbonate (1.69 ml, 7.39 mmol) was added thereto, and they were stirred at room temperature overnight. The reaction mixture was diluted in dichloromethane, washed with water, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate=5/1) to give the titled compound (2.3 g) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 4.74 (s, 1H), 3.80 (m, 2H), 3.67 (m, 1H), 3.54 (m, 1H), 2.82 (s, 3H), 2.71 (m, 4H), 2.04 (m, 2H), 1.85 (m, 2H), 1.71 (m, 1H), 1.59 (m, 1H), 1.48 (s, 9H).

According to the analysis of related databases, 1127-85-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUHAN CORPORATION; SIM, Jae Young; CHA, Myung; KIM, Tae Kyun; YOON, Young Ae; KIM, Dong Hoon; (59 pag.)US2016/90374; (2016); A1;,
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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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, A new synthetic method of this compound is introduced below., 1996-30-1

Carbazole (800 mmol, 133.8 g), 2-bromo-4-chloro-1-fluorobenzene (840 mmol 175.9 g), and dimethylformamide (160 ml) were added to a three-necked flask, and the flask was flushed with nitrogen. Sodium hydride (62% paraffin dispersion) (800 mmol, 31.0 g) was added thereto stepwise five or more times, while observing the amount of hydrogen gas generated, and the reaction mixture was slowly heated while observing the amount of hydrogen gas generated. The reaction mixture was then heated under stirring at a temperature of 150 C. for 20 hours. The reaction mixture was cooled to room temperature, diluted with toluene (1 L), and quenched with a small amount of water in a nitrogen atmosphere. The reaction mixture was filtered by using celite and washed three times with water by using a separatory funnel. The reaction mixture was dried by using anhydrous magnesium sulfate, filtered through a silica gel pad, and then, concentrated. The resultant obtained therefrom was recrystallized in a mixed solvent of ethanol_methanol=1:1 to obtain Intermediate 1-3. The amount of Intermediate 1-3 obtained was 156.1 g and the yield of Intermediate 1-3 was 55%.

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; Samsung Electronics Co., Ltd.; INAYAMA, Satoshi; IRISA, Shiro; KORAI, Keisuke; SAKURAI, Rie; ITO, Mitsunori; NUMATA, Masaki; (265 pag.)US2019/214570; (2019); A1;,
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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. 13526-66-4 name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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. 13526-66-4

To a solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (232.0 mg, 1 .00 mmol) in THF (5 ml_) was added EtMaBr (1 M in THF, 1 .50 ml_, 1 .50 mmol) at -10 QC. After stirring at -10 QC for 1 h, i -methyl-I H-indazole-5-carbaldehyde (240.0 mg, 1.50 mmol) was added. The mixture was allowed to warm to rt slowly and stirred for 2 h. The reaction was quenched with saturated 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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; DAI, Miao; FU, Xingnian; HE, Feng; JIANG, Lei; LI, Yue; LIANG, Fang; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YAN, Xiaoxia; YU, Zhengtian; ZHANG, Ji, Yue; WO2011/20861; (2011); A1;,
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60633-25-2, Name is 2-Bromo-4-chloro-1-methoxybenzene, 60633-25-2, 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.

5-Chloro-2-methoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =Cl) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 2-bromo-4-chloroanisole (2.00 g, 9.0 mmol, 1.0 equivuiv), n-BuLi (2.5M in hexanes; 3.62 mL, 9.0 mmol, 1.0 equivuiv), and trimethylborate (3.0 mL, 26 mmol, 2.9 equivuiv) to afford 1.30 g (77%) of crude 5-chloro-2-methoxyphenylboronic acid as a white semi-solid. This compound was used in the next reaction with no further purification. Methyl (5′-chloro-2′-methoxy-4-nitro-2-biphenyl)carboxylate (structure 39 of Scheme XI, where R1 =H, R2 =Cl)

Statistics shows that 2-Bromo-4-chloro-1-methoxybenzene is playing an increasingly important role. we look forward to future research findings about 60633-25-2.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;,
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13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution under N2 of3-bromo-6-chloro-imidazo[1,2-b]pyridazine (1 g, 4.3 mmol) in dioxane (45 mL), Pd[P(C6H5)3]4(0.248 g, 0.2 mmol), 5-indole-5-boronic acid (0.728 g, 4.51 mmol) and Na2CO3(2 M, 7.7 mL) were added. The mixture was stirred for 21 h at 100 C. Thereaction was monitored by TLC. The solvent was evaporated under reducedpressure. The crude residue was diluted and stirred in AcOEt and ammoniumchloride solution (saturated). The product was extracted with AcOEt, and theorganic layer was washed with NaCl solution. The organic layer was dried overNa2SO4, filtered, and evaporated under reduced pressure.The crude residue was purified by chromatography on silica gel using DCM-AcOEt(6:4) afforded 6a in 72% yield(0.840 g) as a light green powder.

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:
Article; Bendjeddou, Lyamin Z.; Loaec, Nadege; Villiers, Benoit; Prina, Eric; Spaeth, Gerald F.; Galons, Herve; Meijer, Laurent; Oumata, Nassima; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 696 – 709;,
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Adding some certain compound to certain chemical reactions, such as: 933190-51-3, name is 8-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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 933190-51-3. 933190-51-3

[00350] To a 0C mixture of benzyl alcohol (0.3 mL, 2.98 mmol) in THF (40 mL) was added sodium hydride (0.25 g) in an ice-water bath under a N2 atmosphere. The reaction mixture was stirred for 30 minutes at 0C, and then a solution of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (462 mg, 1.99 mmol) in THF (50 mL) was added in dropwise. The reaction mixture was warmed to rt slowly and stirred for 1 hour, then quenched with saturated aqueous sodium chloride solution (50 mL) and the resulting mixture was extracted with ethyl acetate (500 mL). The organic phase was washed with water (50 mL) and saturated aqueous sodium chloride solution (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v) = 1/2) to give the title compound as an oil (0.26 g, 50%). The compound was characterized by the following spectroscopic data:MS-ESI: (ESI, pos.ion)m/z: 260.1 [M+1].

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 8-Bromo-6-chloroimidazo[1,2-b]pyridazine.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CHENG, Changchung; ZHANG, Yingjun; LIU, Bing; LONG, Bohua; CHEN, Yu; CHENG, Zhixin; (182 pag.)WO2016/8433; (2016); A1;,
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33863-76-2, 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 33863-76-2 as follows.

A solution of 1-bromo-3-chloro-5-fluorobenzene (50.0 g, 239 mmol) in DMF (300 ml.) was treated with sodium methoxide (15.5 g, 286 mmol) and the reaction was stirred overnight at rt. The mixture was diluted with ethyl acetate (500 mL) and washed with water (700 mL). The organic layer was isolated, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give 51.0 g of the title compound which was used without purification. 1H NMR (DMSO-c/6) delta 7.23 (t, 1 H), 7.13 – 7.15 (m, 1 H), 7.05 (t, 1 H), 3.77 (s, 3 H).

According to the analysis of related databases, 1-Bromo-3-chloro-5-fluorobenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157273; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 96558-78-0, name is 3-Bromo-5-chlorophenylamine, 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 96558-78-0. 96558-78-0

To a solution of 3 -bromo-5-chloro- aniline (500 mg, 2.42 mmol) in l,4-dioxane (10 ml) and H20 (1 ml) was added 4, 4,5,5- tetramethyl-2-(2-methylprop- l-enyl)- 1 ,3,2-dioxaborolane (529 mg, 2.90 mmol), Pd(dppf)Cl2 (177 mg, 0.24 mmol) and Cs2C03 (2.37 g, 7.26 mmol). The RM was heated to 120 C for 12 h under N2. The solution was concentrated in vacuo. The residue was purified by FCC (25 % EtOAc in petroleum ether) to give the title compound as a green oil (Y = 41 %). ‘H NMR (400 MHz, DMSO-rf6) d ppm 6.42 (t, J= 2 Hz, 1H), 6.37 (s, 1H), 6.34 (s, 1H), 6.08 (s, 1H), 5.35 (s, 2H), 1.83 (s, 3H), 1.80 (s, 3H).

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 3-Bromo-5-chlorophenylamine.

Reference:
Patent; NODTHERA LIMITED; HARRISON, David; WATT, Alan Paul; BOCK, Mark G.; (334 pag.)WO2019/121691; (2019); A1;,
Chloride – Wikipedia,
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60811-21-4,Some common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, molecular formula is C6H3BrClF, 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 dissoprppylamine (5.1 mL, 36.0 mmol, 1.5 eq.) in anhydrous THF (15 mL) was added n-BuLi (19.2 mL, 28.8 mmol, 1.2eq.) dropwise at -78C under N2 atmosphere, then was added the 4-bromo-2-chloro-l-fluorobenzene (5 g, 24.0 mmol, 1.0 eq.) at -78C 1 h later. The mixture was stirred at -78C for 45 minutes, then was added DMF (2.8 mL, 36.0 mmol, 1.5 eq. ), warmed to -30C until TLC showed that the reaction was completed. The reaction was quenched with H20 (100 mL), then adjusted to pH 2-3, extracted with EA (50 mLx3). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and evaporated. The residue was purified by column chromatography (PE/EA=100: 1) to provide 5-bromo-3-chloro-2-fluoroben low solid.

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

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (297 pag.)WO2018/229543; (2018); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

56961-77-4, These common heterocyclic compound, 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, 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.

1-bromo-2,3-dichlorobenzene (15.0 g, 66.4 mmol) and aniline (12.7 g, 136.1 mmol) were added to toluene in a three-necked flask. Dissolved in 450ml sodium tert-butoxide (9.6g, 99.6mmol), bis (tri-tert-butylphosphine) palladium (0) (0.7 g, 1.3 mmol) was added thereto, followed by stirring for 6 hours under reflux conditions under argon atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature, H 2 O was added thereto, and the reaction solution was transferred to a separatory funnel to extract. The extract was dried over MgSO 4, concentrated and the sample was purified by silica gel column chromatography to give 14.7 g of intermediate A-1. (Yield 75%)

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 56961-77-4.

Reference:
Patent; LG Chem, Ltd.; Seo Sang-deok; Park Tae-yun; Lee Dong-hun; (32 pag.)KR2019/141620; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics