Tag: M.W=200-300

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. Computed Properties of C6H3BrClN3

To a solution of 3-bromo-6-chloro-imidazo[1 ,2-b]pyridazine (2.40 g, 10.35 mmol) in 30 ml_ of THF was added EtMgBr (1 M in THF, 12.43 ml_, 12.42 mmol) solution at rt. The solution was stirred for 30 min and a solution of 5,7-difluoroquinoline-6-carbaldehyde (2.0 g, 10.35 mmol) in 1 O mL of THF was added. The resulting mixture was stirred at rt for additional 2 h and then quenched with 50 ml_ of NH4CI solution. The solution was extracted with EtOAc and the combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to afford 3.48 g (97%) of the title compound. LCMS (method B): [MH]+ = 347, tR = 1 .23 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; 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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Electric Literature of 210532-25-5, 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. 210532-25-5 name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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.

General procedure: A mixture of appropriate aryl sulfonyl chloride (0.6mmol), 48 (179.7mg, 0.5mmol), Cs2CO3 (325mg, 1mmol) and acetone (5mL) was stirred at room temperature for overnight. The mixture was filtered to remove Cs2CO3 and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Difluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Wang, Guangcheng; Li, Chunyan; He, Lin; Lei, Kai; Wang, Fang; Pu, Yuzi; Yang, Zhuang; Cao, Dong; Ma, Liang; Chen, Jinying; Sang, Yun; Liang, Xiaolin; Xiang, Mingli; Peng, Aihua; Wei, Yuquan; Chen, Lijuan; Bioorganic and Medicinal Chemistry; vol. 22; 7; (2014); p. 2060 – 2079;,
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Synthetic Route of 1940-27-8, A common heterocyclic compound, 1940-27-8, name is 4-Bromo-2,5-dichloroaniline, molecular formula is C6H4BrCl2N, 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 compound (III) (4.2 mmol), the appropriate amine (4.2 mmol) and triethylamine (8.4mmol) in dry acetonitrile was refluxed for 3 hr. The mixture was cooled, poured on crushed ice and filtered. The residue was washed with cold water and dried. The crude product was recrystallized from ethanol to get the titled compounds.

The synthetic route of 1940-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pradeep Kumar; Joshi, Shrinivas D.; Dixit, Sheshagiri R.; Kulkarni; Indian Journal of Heterocyclic Chemistry; vol. 25; 1; (2015); p. 37 – 44;,
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Electric Literature of 110407-59-5, The chemical industry reduces the impact on the environment during synthesis 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, I believe this compound will play a more active role in future production and life.

Step 1: Synthesis of l-bromo-2-chloro-4-methylsulfanylbenzene. (8)[00392] A solution of l-bromo-2-chloro-4-fluorobenzene (7, 0.50 g, 2.39 mmol) and sodium thiomethoxide (0.17 g, 2.42 mmol) in DMSO (2.5 mL) was stirred at 100 C for 1 h. The reaction mixture was added to 20 mL water with stirring, the aqueous mixture was extracted with ethyl acetate (2 x 20 mL) and the combined organic layers were dried over sodium sulfate, filtered and evaporated in vacuo. The title compound (0.62 g) was obtained as a colorless oil and was used in the next step without further purification.

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-Chloro-4-fluorobromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio, G.; VOLLRATH, Benedikt; WADE, Warren; WO2011/156646; (2011); A2;,
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Adding a certain compound to certain chemical reactions, such as: 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, 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 1996-30-1, Recommanded Product: 3-Bromo-4-fluorochlorobenzene

890 p1 (7.0 mmol) of 2-bromo-4-chloro-1-fluorobenzene, 720 mg (7.02 mmol) of 4-chloro-1H- imidazole, 2.91 g (21.1 mmol) of potassium carbonate and 30 ml DMF were divided into twomicrowave vessels and stirred in the microwave at 130C for 3 hours. After cooling, the two reaction mixtures were combined and 150 ml of cold water were added with stirring. This mixture was stirred for 5 mm. The suspension was then filtered and the solid was washed with ice-water and pentane and dried under high vacuum. Yield: 1.33 g (64% of theory)LC/MS [Method 1]: R = 0.97 mm; MS (ESIpos): m/z = 293 (M+H),?H-NMR (400 MHz, DMSO-d6): oe [ppm] = 8.05 (d, 1H), 7.89 (d, 1H), 7.68-7.59 (m, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-fluorochlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; JIMENEZ NUNEZ, Eloisa; ACKERSTAFF, Jens; ROeHRIG, Susanne; HILLISCH, Alexander; MEIER, Katharina; HEITMEIER, Stefan; TERSTEEGEN, Adrian; STAMPFUSS, Jan; ELLERBROCK, Pascal; MEIBOM, Daniel; LANG, Dieter; (399 pag.)WO2017/5725; (2017); A1;,
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50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, 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. COA of Formula: C7H6BrClO

EXAMPLE 21 Preparation of 5-Hydroxy-3-(3-chloro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-cyclopent-2-en-1-one of Formula (67) [0134] A mixture of magnesium turnings (0.31 g, 13.1 mmol), 2-chloro-4-bromoanisole (3.00 g, 13.5 mmol), 4-tert-butyldimethysilyloxy-2-(3,4,5-trimethoxy-phenyl)-cyclopent-2-en-1-one (2.58 g, 6.84 mmol) and dry tetrahydrofuran (35 ml) under nitrogen was stirred at room temperature for 4 h. Reaction was then quenched with dil hydrochloric acid (30 ml), tetrahydrofuran was removed under reduced pressure and the residual reaction mixture was extracted with ethyl acetate (3*35 ml), washed with water (2*20 ml) and dried over sodium sulfate. Concentration and purification by column chromatography over silica gel (eluent-6% acetone in pet ether) afforded the alcohol of the formula (4A) [0135] wherein R1=R5=R6=R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl (1.32 g, 37%). [0136] A solution of the above alcohol of the formula (4A) wherein R1=R5=R6 =R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl wherein (0.95 g, 1.83 mmol) in dry dichloromethane (15 ml) was cooled to 0 C., pyridinium dichromate (1.92 g, 8.17 mmol) was added and the mixture was stirred at room temperature for 3 h. Filtration through celite (3.00 g), washing with dichloromethane (30 ml) and concentration afforded the crude product which was purified by silica gel column chromatography (eluent-3% acetone in pet ether) to yield the title compound of the formula (1B) wherein R=OTBS, R1=R5=R6=R7=R10=H, R2=R3=R4=R8=OMe, R9=Cl (0.32 g, 34%), which on deprotection of TBDMS group using the procedure described in example 10 furnished the compound of formula (67). [0137] Spectral data of compound of the formula of structure (67) [0138] 1H NMR(CDCl3+CCl4): delta 2.96 (dd, J=18 Hz and 2 Hz, 1H), 3.33 (dd, J =18 Hz and 6 Hz, 1H), 3.75 (s, 6H), 3.86 (s, 3H), 3.91 (s, 3H), 4.45-4.54 (m, 1H), 6.42 (s, 2H), 6.81 (d, J=8 Hz, 1H), 7.21-7.29 (m, 1H), 7.48 (bs, 1H). [0139] 13C-NMR (CDCl3+CCl4): delta 37.79, 55.87 (2C), 60.58, 71.57, 106.23 (2c), 111.31, 122.41, 126.82, 127.59, 128.58 (2C), 130.05, 135.90, 138.07, 153.36 (2C), 156.48, 162, 51, 206.95

The synthetic route of 50638-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DABUR RESEARCH FOUNDATION; WO2004/56738; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

93765-83-4, name is 1-Bromo-5-chloro-2-fluoro-4-methylbenzene, 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. Safety of 1-Bromo-5-chloro-2-fluoro-4-methylbenzene

To a solution of 1-bromo-5-chloro-2-fluoro-4-methylbenzene (11.3 g, 50 mmol) in dry THF (100 mL) was added isopropylmagnesium chloride (30 mL, 2 M) dropwise. After stirring at room temperature for 30 min, dry CO2 was added and the mixture was stirred at room temperature for additional 30 min. The reaction was quenched by sat. NH4Cl and extracted with EtOAc (100 mL*3). The combined organic layers were washed with water (50 mL*3), dried over anhydrous Na2SO4, filtered and concentrated to give the desired product (4.7 g, 49%). LCMS (ESI) m/z: 187.0 [M-H]-.

The synthetic route of 93765-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENON PHARMACEUTICALS INC.; GENENTECH, INC; Chowdhury, Sultan; Dehnhardt, Christoph Martin; Focken, Thilo; Grimwood, Michael Edward; Hemeon, Ivan William; Jia, Qi; Ortwine, Daniel; Safina, Brian; Sun, Shaoyi; Sutherlin, Daniel P.; Zenova, Alla Yurevna; US2013/317000; (2013); A1;,
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Related Products of 69695-61-0, These common heterocyclic compound, 69695-61-0, name is 2-Chloro-4-(trifluoromethoxy)aniline, 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.

An aqueous solution of 2-chloro-4-(trifluoromethoxy)phenylamine (9.0 g) was cooled at 0C, and concentrated hydrochloric acid (75 mL) was dropped slowly to its solution. The reaction mixture was stirred for 30 minutes, and sodium nitrite (3.73 g) was added to the reaction mixture. The reaction mixture was stirred for 40 minutes. An aqueous mixture solution of copper cyanide (4.65 g) and sodium cyanide (7.08 g) which been cooled off in 0C was added to the reaction mixture, and the reaction mixture stirred at room temperature for an hour. The reaction mixture was poured into 5N aqueous solution of sodium hydroxide which been cooled with ice, and extracted twice with ethyl acetate. The organic layer was washed by a saturated aqueous solution of sodium chloride, and dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (high flash-SI, size 4L (made in Yamazen corporation), n-hexane?ethyl acetate/n-hexane=1/8) to obtain a title compound (7.36 g) having the following physical data. TLC:Rf 0.50 (n-hexane/ethyl acetate=20/1); 1H-NMR(CDCl3): delta 7.18 (m, I H), 7.37 (m, 1 H), 7.72 (d, J=8.6 Hz, 1 H).

The synthetic route of 69695-61-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO Pharmaceutical Co., Ltd.; EP2154139; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 69695-61-0 as follows. Recommanded Product: 69695-61-0

(e) Preparation of 5-Methanesulfonyl-pyridine-2-carboxylic acid (2-chloro-4-trifluoromethoxy- phenyl)-amide 7:2-Chloro-4-trifluoromethoxy-phenylamine (2.0 g, 9.29 mmol) in toluene (50 mL) was added to trimethylaluminum (2.0 M 4.65 mL) then methyl 5-(methylsulfonyl)picolinate 6 (1.0 g, 4.65 mol) was added and the mixture was heated to 80-90C for 2 h. The reaction was cooled down and IN HC1 solution (10 mL) was added to be acidic. Dichloromethane (100 mL) was then added and the organic phase was further washed with water (100 mL) and dried over sodium sulfate. The solvent was removed and the residue was mixed with ether (50 mL) and stirred for 0.5 h. The solid was filtered and dried to give 5-methanesulfonyl-pyridine-2-carboxylic acid (2- chloro-4-trifluoromethoxy-phenyl)-amide 7 as a light yellow solid. Yield: 1.26 g, 65%.1H-NMR (300 Hz, CDCI3) delta (ppm): 10.6 (s, 1H), 9.21 (m, 1H), 8.68 (dd, 1H), 8.52 (dd, 1H), 7.40 (dd, 1H),7.22 (m, 2H), 3.20 (s, 3H).

According to the analysis of related databases, 69695-61-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OSLO UNIVERSITY HOSPITAL HF; HOLSWORTH, Daniel; WAALER, Jo; MACHON, Ondrej; KRAUSS, Stefan; VORONKOV, Andrey Edward; GOLDING, Louise; WO2012/76898; (2012); A1;,
Chloride – Wikipedia,
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873-38-1, name is 2-Bromo-4-chloroaniline, 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. Application In Synthesis of 2-Bromo-4-chloroaniline

4-chloro-2-bromo-aniline (206 mg, 0.01 mmol) was dissolved in dimethylsulfoxide (20 mL). Under a nitrogen atmosphere, bis(pinacolato)diboron (3.8 g, 15 mmol), potassium acetate (2.5 g, 25.7 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (218 mg, 0.3 mmol) were added thereto, and the temperature was raised to 80 C. to allow the reaction to proceed for 24 hours. Water (100 ml) was added to the reaction solution, which was extracted with ethyl acetate (80 ml¡Á2). The organic phases were combined, washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:100 to 1:30) to give the title compound 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2i) as a white solid (2.0 g, yield 79%). 1H NMR (400 MHz, CDC3) delta 7.54 (s, 1H), 7.19-7.08 (m, 1H), 6.55 (d, 1H), 4.86 (s. 2H), 1.34 (s, 12H). LCMS m/z=254.0 [M+1].

The synthetic route of 873-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; Wei, Yonggang; QIU, Guanpeng; ZHENG, Suxin; LEI, Bolin; YU, Yan; CHEN, Yashu; (29 pag.)US2017/29423; (2017); A1;,
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