Tag: M.W=200-300

Reference of 1205-71-6, These common heterocyclic compound, 1205-71-6, name is 4-Chloro-N-phenylaniline, 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.

In a 250 ml round bottom flask, 8-bromobenzo [b] naphtho [2,1-d] thiophene (12 mmol), copper iodide (15 mmol), potassium tert-butoxide (65 mmol), 1,2-di Aminocyclohexane (12 mmol) and (12 mmol) (3-chloro-phenyl) -phenylamine were added to dry 1,4-dioxane (100 ml), and the mixture was refluxed under N2 atmosphere for 48 hours. The intermediate was cooled to room temperature, added to water, and then filtered through a pad of celite while extracting with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate. After filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain Intermediate HT042-1.

Statistics shows that 4-Chloro-N-phenylaniline is playing an increasingly important role. we look forward to future research findings about 1205-71-6.

Reference:
Patent; Shanghai Tianma Organic Shine Display Co., Ltd.; Zhang Lei; Gao Wei; Niu Jinghua; Dai Wenpeng; Xiao Wenjing; Lu Yan; Zhu Hongyan; (28 pag.)CN110746391; (2020); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 39226-96-5, 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. 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 2a (438mg, 2.5mmol) and 2-chloro-3-(trifluoromethyl)benzylamine (419mg, 2.0mmol) were mixed with EDAC (480mg, 2.5mmol) and 1-hydrobenzotrizole (HOBt, 338mg, 2.5mmol) in dry dichloromethane (60mL). The reaction mixture was stirred for overnight at RT. Then the resultant mixture was washed with 2N HCl (50mL) and saturated aqueous NaHCO3 (40mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel with eluent (2:98 MeOH/CH2Cl2) to afford a white solid product 3a (210mg, 28%), Rf=0.34 (1:15 MeOH/CH2Cl2), mp 147-149C. 1H NMR (CDCl3): delta 2.03-2.09 (m, 1H, CH), 2.31-2.40 (m, 2H, CH2), 2.49-2.57 (m, 1H, CH), 3.21-3.30 (m, 1H, CH), 3.80 (dd, J=15.5, 36.0Hz, 1H, CH), 4.22 (dd, J=4.0, 8.0Hz, 1H, CH), 4.45-4.58 (m, 2H, CH2), 4.61 (d, J=6.0Hz, 2H, CH2Ph), 6.53 (br s, 1H, CONH), 7.37 (t, J=8.0Hz, 1H, Ph-H), 7.59 (d, J=8.0Hz, 1H, Ph-H), 7.66 (d, J=8.0Hz, 1H, Ph-H). 1C NMR (CDCl3): delta 23.96, 29.51, 41.92, 42.67 (d, JC-F=18.75Hz), 62.55 (d, JC-F=1.25Hz), 82.36 (d, JC-F=166.25Hz, CH2F), 119.66 (q, JC-F=271.25Hz, CF3), 127.11, 127.31 (q, JC-F=5.0Hz), 129.05 (q, JC-F=30.0Hz), 131.85, 133.92, 137.73, 171.51, 176.21. MS (ESI): 367 ([M+H]+, 100%); MS (ESI): 365 ([M-H]-, 50%). HRMS (ESI): calcd for C15H16N2O2ClF4 ([M+H]+) 367.0836, found 367.0848.

The synthetic route of (2-Chloro-3-(trifluoromethyl)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Mingzhang; Wang, Min; Glick-Wilson, Barbara E.; Meyer, Jill A.; Peters, Jonathan S.; Territo, Paul R.; Green, Mark A.; Hutchins, Gary D.; Zarrinmayeh, Hamideh; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 9; (2018); p. 1603 – 1609;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 51419-59-1, name is p-Tolylmethanesulfonyl chloride, 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 51419-59-1, HPLC of Formula: C8H9ClO2S

The product of step (v) (360 mg) was dissolved in DCM (5 ml), this was followed by addition of a solution of NaHCO3 (218 mg) in water (5 ml). (4-methylphenyl)methane sulfonyl chloride (280 mg) was added portionwise and stirred for 1 day, then additional NaHCO3 and sulfonyl chloride were added and stirred for 3 days overall. The reaction was diluted with water and extracted with DCM (.x.3). The combined organic layers were washed (brine), dried (MgSO4) then concentrated under reduced pressure to give the sub-title compound as a pale yellow oil, yield 210 mg.MS: ESI(+ve) 479 (M+H)

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, p-Tolylmethanesulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2008/255150; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 933190-51-3,Some common heterocyclic compound, 933190-51-3, name is 8-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.

Benzyl alcohol (0.3 mL, 2.98 mmol) was dissolved in tetrahydrofuran (40 mL) under nitrogen and cooled to 0 C in an ice water bath. Sodium hydride (0.25 g) was added and the solution was stirred at 0 for 30 min. 8-bromo-6-chloroimidazo[1,2-b]pyridazine (462 mg, 1.99 mmol) in tetrahydrofuran (50 mL) was added dropwise and the mixture was slowly returned to room temperature and stirred for 1 h.The reaction was quenched with saturated sodium chloride solution (50 mL), extracted with ethyl acetate (500 mL), washed with organic phase (50 mL) and saturated sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure and the residue was subjected to column chromatography (V (ethyl acetate) / V (petroleum ether) = 1/2) to give 0.26 g of an oily product in a yield of 50%.

The synthetic route of 933190-51-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CHENG, CHANGCHUNG; ZHANG, YINGJUN; LIU, BING; LONG, BOHUA; CHEN, YU; CHENG, ZHIXIN; (202 pag.)TW2017/6256; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, A new synthetic method of this compound is introduced below., Product Details of 13745-86-3

2-Amino-2′-carboxydiphenylsulphide (100 g) was taken in phosphorus oxychloride (500 ml). The reaction mixture was heated to reflux at 105-110C for 5-6 hours. The reaction mixture was subjected to vacuum distillation to remove unreacted phosphorous oxychloride. The resulting mass was taken in toluene (800 ml) and piperazine (210g) was added. The reaction mixture was heated to reflux at 110-120C for 6-8 hours. The reaction mixture was cooled, filter and the organic phase was washed with water, dried and solvent was distilled off under vacuum to obtain the title compound.

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; JUBILANT ORGANOSYS LIMITED; WO2006/27789; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 96558-78-0, 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. 96558-78-0 name is 3-Bromo-5-chlorophenylamine, 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.

To a solution of 3-bromo-5-chloro-aniline (2 g, 9.7 mmol, 1 eq), 2,3-dihydrofuran (1.4 g, 19.4 mmol, 1.5 mL, 2 eq), PPI13 (508.3 mg, 1.9 mmol, 0.2 eq) and K2CO3 (4.0 g, 29.1 mmol, 3 eq) in 20 mL of DMF was added Pd(OAc)2 (217.6 mg, 969.0 pmol, 0.1 eq) at 20C under N2. The mixture was stirred at 110C for 12 hours. Then it was partitioned between 20 mL of water and 40 mL of ethyl acetate. The organic phase was separated, washed with 60 mL of brine, dried over Na2SC>4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography (S1O2, Petroleum ether : Ethyl acetate = 100: 1 to 10: 1) to give 780 mg of compound 2A (4.0 mmol, 41.1% yield) as a yellow oil and 470 mg of compound 2B (2.4 mmol, 24.8% yield) as a yellow oil

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

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; VACCA, Joseph, P.; WAGER, Travis, T.; (383 pag.)WO2020/117877; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 30273-47-3, name is 4-Bromo-5-chloro-2-methylaniline, 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. Computed Properties of C7H7BrClN

Example 11; 3-(4-(5-(8-Bromo-6-(trifluor omethv l)im idazo [ 1 ,2-alpha] pyridin-2-yl)- 1 ,2,4-oxadiazol-3-yl)-2- chloro-5-methylphenyl)propanoic acid; 2-Methyl-4-bromo-5-chloro benzonitrile (57).; To a stirred solution of 2-methyl-4- bromo-5-chloro aniline (56) (2.9 g, 13 mmol) in concentrated HCl (14.5 rnL) cooled to 0 0C was added a solution of sodium nitrite (1 g, 14 mmol) in water (3.5 mL) slowly over 20 min. After stirring at 0 0C for 35 min, a pre-cooled solution of copper (I) cyanide (11.80 g, 13.1 mmol) and sodium cyanide (6.46 g, 13.1 mmol) in water (81 mL) was gradually added to the above solution of diazonium salt at 0 0C over a period of 50 min. After addition, the resulting mixture was stirred at room temperature for 18 h. The precipitated solid was filtered, washed with water and dried. The resulting solid was then dissolved in EtOAc and washed with water followed by saturated NaCl solution. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography, eluting with 5-10% EtOAc/hexane, to afford the title intermediate 57 as a white solid (2.1 g, yield 69%).

The synthetic route of 4-Bromo-5-chloro-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; CANNE BANNEN, Lynne; CHAN, Diva Sze-ming; GU, Xiao-hui; MAC, Morrison, B.; NG, Stephanie; WANG, Tie-lin; WANG, Yong; XU, Wei; WO2010/65760; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 20816-79-9, A common heterocyclic compound, 20816-79-9, name is 1-Bromo-8-chloronaphthalene, molecular formula is C10H6BrCl, 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.

To a solution of benzyl (2S)-2-(cyanomethyl)-4-[2-[[(2,S)-l – methylpyrrolidin-2-yl]methoxy]-6,7,8,9-tetrahydro-5/7-pyrimido[4,5-c]azepin-4-yl]piperazine-l – carboxylate (250 mg. 481 pmol, 1.0 eq) and l-bromo-8-chloro- naphthalene (232 mg, 962 pmol, 2.0 eq) in toluene (4.0 mL) was added RuPhos (89.8 mg, 192 pmol, 0.4 eq), CS2CO3 (392 mg, 1.20 mmol, 2.5 eq) and Pd2(dba)3 (88.1 mg, 96.2 pmol, 0.2 eq), the reaction mixture was stirred at 90 C for 10 hours under N2. After completion, the reaction mixture was filtered through a celite, the filter cake was washed with ethyl acetate (10 mL), and adjusted with 1N HC1 aqueous to pH~3, the organic layer was separated, and the aqueous was adjusted with Na2C03 solid to pi 1 8. extracted with ethyl acetate (2 x 10 mL), the organic layer was washed with saturated brine (1 c 20 mL), dried over Na2S04, filtered and concentrated. The residue was purified by reverse phase flash (Cl 8, 0.1 %FA in water, 30%-50% MeCN). The product benzyl (25 -4-[8-(8- chloro-l-naphthyl)-2-[[(25)-l -methylpyrrolidin-2-yl] methoxy]-5,6,7,9-tetrahydropyrimido[4,5- c]azepin-4-yl]-2-(cyanomethyl)piperazine-l-carboxylate (130 mg, 185 pmol, 38% yield, 97% purity) was obtained as yellow solid. LCMS [ES1, M+l]: 680. (0587) [0348] NMR (400 MHz, chloroform-d) d 7.74 – 7.68 (m, 1H), 7.59 – 7.51 (m, 1H), 7.48 – 7.15 (m, 9H), 5.21 (s, 2H), 4.74 – 4.63 (m, 1H), 4.40 – 4.29 (m, 211), 4.21 – 4.05 (m, 211), 3.84 – 3.71 (m, 1 H), 3.69 – 3.46 (m, 2H), 3.44 – 3.15 (m, 3LI), 3.13 – 2.60 (m, 8H), 2.46 (s, 3H), 2.33 – 2.21 (m, 1 H), 2.17 – 2.02 (m, 2H), 1.96 – 1.72 (m, 4H). LCMS [ESI, M+l]: 546.

The synthetic route of 20816-79-9 has been constantly updated, and we look forward to future research findings.

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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 699-89-8, name is 4,7-Dichlorothieno[2,3-d]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., name: 4,7-Dichlorothieno[2,3-d]pyridazine

One equivalent of dichloride (1) and 2.2 equivalent of M-NH2 are refluxed in an appropriate amount of n-butanol at 150C for 10 hrs. The reaction mixture is allowed to cool to room temperature and the precipitate (4) that forms is filtered and washed sequentially with isopropyl alcohol, 4.0 N KOH, H2O, and hexane, and then dried. The crude product (4) is purified by preparative TLC or flash chromatography on silica gel using dichloromethane/methanol (95:5) as the eluent. Final product is confirmed by LC/MS and/or NMR. The invention compounds of Examples 26 – 33 and 75 as shown in the below table were prepared by method A-2.

According to the analysis of related databases, 699-89-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CORPORATION; EP1228063; (2009); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 883499-24-9, 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. 883499-24-9, name is 1-Bromo-2-chloro-3-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of l-brmo-2-chloro-3-fluoro benzene (1.0 g, 4.79 mmol) in toluene (20mL) were added phenyl boronic acid(875 mg, 7.18 mmol), Na2C03 (1.52 g, 14.35 mmol),water (5 mL) and degassed for 10 min in argon atmosphere. Then to it was added Pd(PPh3)4 (553 mg, 0.48 mmol) and again degassed for 5 min. The reaction was heated to 100C for 16 h. The reaction mixture was then cooled to 25C, filtered through celite and washed with ethyl acetate. The separated organic layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to get the crude product which was purified by combiflash column chromatography using hexane to get 2-chloro-l-fluoro-3- phenylbenzene (920 mg, 93%) as yellow, sticky liquid.

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, 1-Bromo-2-chloro-3-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ALANINE, Alexander; AMREIN, Kurt; BLEICHER, Konrad; FASCHING, Bernhard; HILPERT, Hans; KOLCZEWSKI, Sabine; KROLL, Carsten; SCHAEUBLIN, Adrian; ZAMPALONI, Claudia; (176 pag.)WO2018/189065; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics