Tag: M.W=200-300

Related Products of 57310-39-1, A common heterocyclic compound, 57310-39-1, name is 3-Bromo-4-chlorotoluene, molecular formula is C7H6BrCl, 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.

The title compound was prepared from 39 in the same manner as described for 33 (63% yield over two steps, a colorless oil).1H NMR (CDCl3) delta: 2.31 (3H, s), 3.58-3.90 (6H, m), 3.96 (1H, d, J = 10.6 Hz), 4.38 (1H, d, J = 10.4 Hz), 4.50-4.68 (3H, m), 4.78-4.98 (4H, m), 6.91-7.08 (3H, m), 7.12-7.38 (20H, m). MS (FAB) m/z: 649 (M++H), calcd for C41H41ClO5: 648.

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:
Article; Ikegai, Kazuhiro; Imamura, Masakazu; Suzuki, Takayuki; Nakanishi, Keita; Murakami, Takeshi; Kurosaki, Eiji; Noda, Atsushi; Kobayashi, Yoshinori; Yokota, Masayuki; Koide, Tomokazu; Kosakai, Kazuhiro; Ohkura, Yasufumi; Takeuchi, Makoto; Tomiyama, Hiroshi; Ohta, Mitsuaki; Bioorganic and Medicinal Chemistry; vol. 21; 13; (2013); p. 3934 – 3948;,
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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 30273-47-3 as follows. Product Details of 30273-47-3

First, into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed dichloromethane (400 mL), 4-bromo-5-chloro-2-methylaniline (25 g, 113.38 mmol, 1.00 equiv). This was followed by the addition of TFAA (trifluoroacetic anhydride, 27.4 g, 130.46 mmol, 1.15 equiv) dropwise with stirring at 0 C. in a water/ice bath. The resulting solution was allowed to react, with stirring, for an additional 1 h at room temperature. The resulting mixture was concentrated under vacuum. This resulted in 30 g (84%) of N-(4-bromo-5-chloro-2-methylphenyl)-2,2,2-trifluoroacetamide as a white solid. First, a solution of 4-bromo-5-chloro-2-methylaniline (5 g, 22.68 mmol, 1.00 equiv), TFAA (5.5 g, 26.19 mmol, 1.50 equiv) in dichloromethane (50 mL) was placed into a 100-mL round-bottom flask. The resulting solution was stirred for 4 h at room temperature. The resulting mixture was concentrated under vacuum. This resulted in 7.9 g (crude) of N-(4-bromo-5-chloro-2-methylphenyl)-2,2,2-trifluoroacetamide as a brown solid.

According to the analysis of related databases, 30273-47-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERIAL, INC.; Meng, Charles; Le Hir de Fallois, Loic; (40 pag.)US2015/366198; (2015); 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. 823-57-4, name is 2-Bromo-5-chloroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 823-57-4

General procedure: To a solution of 2-bromoaniline (1.0 equiv.) and N,N-diisopropylethylamine (2.4 equiv.) in toluene was added cis-1,4-dichlorobut-2-ene (1.8 equiv.). The mixture was stirred at reflux until complete consumption monitored by TLC. The reaction was cooled to room temperature, diluted with water, and extracted with EtOAc. The combined organic layers were washed with saturated NaCl solution and dried over Na 2 SO 4 . The solvents were removed under reduced pressure, purified by flash chromatography to give the pure or crude desired product 3. The product 3 was dissolved in anhydrous THF, then was cooled to -78 oC, n-BuLi (1.2 equiv., 2.5 mol/L in n-hexane) was added dropwise to the mixture and keep temperature no more than -50 oC, the mixture was stirred for 30 minutes, (COOR3) 2 (1.0-1.2 equiv.) in THF was added dropwise at -78 oC and stirred at -78 oC for 2 h. The reaction was warmed to room temperature slowly, then quenched with saturated NH 4 Cl solution, and extracted with EtOAc. The combined organic layers were washed with saturated NaCl solution and dried over Na 2 SO 4 . The solvents were removed under reduced pressure, purified by flash chromatography to give the desired product 1.

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:
Article; Du, Hong-Jin; Lin, Chao; Wen, Xiaoan; Xu, Qing-Long; Tetrahedron; vol. 74; 52; (2018); p. 7480 – 7484;,
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Reference of 2770-11-8, These common heterocyclic compound, 2770-11-8, name is 2-(4-Chlorophenoxy)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.

A solution of the aniline (250 mg, 1.14 mmol), l-acetyl-3-indolecarboxaldehyde (107 mg, 0.57 mmol), NaBH(OAc)3 (302 mg, 1.43 mmol) and AcOH (205 mg, 3.42 mmol) in 1,2-DCE (3 ml) was stirred at room temperature for 16 h. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate (5 ml) and extracted with EtOAc (3 x 5 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo before purification by flash chromatography (eluant; 8:2 hexane:EtOAc to EtOAc) proceeded to afford the desired product which was recrystallised from EtOAc and hexane to afford a cream solid (174.1 mg, 78%).1H NMR: (CDCl3, 270 MHz): delta 2.56 (3H, s, CH3), 3.77 (IH, br s, NH), 4.47 (2H, br s,CH2), 6.65-7.50 (12H, m, ArH), 8.41 ppm (IH, d, J= 7.9 Hz, ArH). 13C NMR: (CDCl3, 67.93 MHz): 5 24.1, 39.7, 112.1, 117.0, 117.6, 118.5, 119.0, 119.6,120.1, 123.0, 123.7, 125.5, 125.7, 128.0, 129.7, 136.1, 140.0, 143.5, 156.2, 168.6 ppm.LCMS: 1.550 min, (95% MeOH : 5% water at 1.0 ml/min), AP”: 389.20.HPLC: 3.410 min, 95.90% purity, (isocratic, 90% acetonitrile : 10% water at 1.0 ml/min).HRMS (MicroTOF): C23H20ClN2O2 requires 391.1208, found 391.1194. M.Pt. 107-1080C.

Statistics shows that 2-(4-Chlorophenoxy)aniline is playing an increasingly important role. we look forward to future research findings about 2770-11-8.

Reference:
Patent; STERIX LIMITED; WO2009/66072; (2009); A2;,
Chloride – Wikipedia,
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Reference of 57310-39-1, 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 57310-39-1 as follows.

Step 1: Synthesis of 1-bromo-2-chloro-5-methyl-4-nitrobenzene (8A) A solution of compound 2-bromo-1-chloro-4-methylbenzene (50 g, 0.24 mol, 1 eq) in conc.H2SO4 (400 ml), was cooled to 0-5 C. using an ice-water-methanol bath. Fuming nitric acid (10.38 ml, 1.48 g/ml, 0.24 mol) in con.H2SO4 (26 ml) was slowly added dropwise to the mixture and then stirred at 0 C. for 3 h. The solution was poured into 500 g ice/water and extracted with dichloromethane (2*300 mL). The combined organic layers were washed with water, dried over Na2SO4 and concentrated to give 58 g of 8A which was used the next step directly without further purification. 1H NMR (400 MHz, DMSO-d6) delta 8.09 (s, 1H), 7.64 (s, 1H), 2.57 (s, 3H).

According to the analysis of related databases, 57310-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio G.; US2013/116263; (2013); A1;,
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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. 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C7H6BrCl

General procedure: Nitrogen was purged through a stirred solution of 4-bromo-1-chloro-2-methylbenzene (258muL, 1.95mmol) in 1,4-dioxane (5mL) for 30min rac-BINAP (363mg, 1.95mmol), caesium carbonate (1.27g, 3.89mmol), 1-Boc-piperazine (363mg, 1.95mmol) and Pd(OAc)2 (87mg, 0.039mumol) and stirred at reflux for 14h under N2. The reaction was filtered through celite and concentrated in vacuo. The residue was dissolved in EtOAc (20mL), filtered through celite and washed with additional EtOAc (50mL). The organic layer was washed with water (2×20mL) and brine (2×20mL), dried with Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (100% CyHex to 10% EtOAc/CyHex) to obtain the protected intermediate as a solid (413mg, 68%). MS, m/z=255 (100) [M-tBu]. The intermediate was dissolved in a 1:3 mixture of TFA/DCM (4mL) and stirred at 20C for 1h. The solvent was evaporated in vacuo and the crude residue dissolved in EtOAc (10mL) which was successively washed with a 10% solution of NaHCO3 (10mL), water (10mL) and brine (10mL). The organic layer dried with Na2SO4 and concentrated in vacuo to obtain 92 as a solid (211mg, 76%). 1H NMR (300MHz; CDCl3): delta 7.23 (d, J 8.8Hz, 1H), 6.80 (d, J 2.9Hz, 1H), 6.71 (dd, J 3.0, 8.7Hz, 1H), 3.35-3.19 (m, 8H), 2.35 (s, 3H). MS, m/z=211 (100) [M+H]+, 213 (30).

The synthetic route of 54932-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Blackmore, Timothy R.; Jacobson, Jonathan; Jarman, Kate E.; Lewin, Sharon R.; Nguyen, William; Purcell, Damian F.; Sabroux, Helene Jousset; Sleebs, Brad E.; European Journal of Medicinal Chemistry; vol. 195; (2020);,
Chloride – Wikipedia,
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Reference of 38762-41-3, 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 38762-41-3 as follows.

8-(4-Bromo-2-chloro-phenylamino)-imidazo[l,5-alpyridine-7- carboxylic acid methyl ester[00245] A suspension of 8-chloro-imidazo[ 1 ,5-a]pyridine-7-carboxylic acid methyl ester(300 mg, 1.43 mmol), 4-bromo-2-chloroaniline (354 mg, 1.72 mmol), Pd2dba3 (65 mg, 0.07 mmol), 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (131 mg, 0.28 mmol) and K3PO4 (424 mg, 2.00 mmol) in toluene (5 ml) was degassed and then heated at HO0C for 18 hours. The reaction mixture was then cooled to room temperature and diluted with ethyl acetate. The resultant mixture was washed with water and brine, then loaded onto a 10 g Isolute SCX-2 cartridge which was eluted with methanol and then a 2M solution of ammonia in methanol. The appropriate fractions were combined and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si-PPC, gradient 0% to 100%, ethyl actetate in DCM) to afford the title compound as a yellow oil (271 mg, 50%). LCMS (method B): Rx = 3.65 min, [M+H]+ = 381/383.

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; WO2009/85980; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13526-66-4, These common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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.

Preparation of trans-4-(3-bromoimidazo[1,2-b]pyridazin-6-ylamino)cyclohexanol To 6-chloro-3-bromoimidazo[1,2-b]pyridazine (1.00 g, 4.30 mmol, 1.0 equiv) and p-TSA (818 mg, 4.30 mmol, 1.0 equiv) in DMSO (7.00 mL) was added trans-4-aminocyclohexanol (1.49 g, 12.9 mmol, 3.0 equiv). The mixture was heated at 100 C. for 24 h. Purification by column chromatography using 5% methanol in dichloromethane elution gave 1.1 g of the yellow solid, 83%.

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Califia Bio, Inc.; GOODFELLOW, VAL S.; NGUYEN, THONG X.; RAVULA, SATHEESH B.; GELBARD, HARRIS A.; US2014/256733; (2014); A1;,
Chloride – Wikipedia,
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Electric Literature of 57310-39-1,Some common heterocyclic compound, 57310-39-1, name is 3-Bromo-4-chlorotoluene, molecular formula is C7H6BrCl, 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.

Example 7: 4-(2′-Chloro-5′-methyl-biphenyl-4-ylmethyl)-2-phenyl-morpholine; 109mg of 4-(4-Bromo-benzyl)-2-phenyl-morpholine was combined with 102mg of bis(pinacolato)diboron, 97mg of potassium acetate, l lmg tetrakis(triphenylphosphine)palladium(0), and 1.9mL DMF. The mixture was heated in a microwave reactor at 12O0C for 7 minutes and cooled. 0.8mL of 2M aqueous sodium bicarbonate was added along with lOlmg of 3-Bromo-4-chlorotoluene in 0.15mL DMF. The mixture was heated in the microwave reactor for an additional 5 minutes at 120C. The reaction was cooled and filtered through Celite, washing with methylene chloride. The eluant was concentrated and purified by flash chromatography twice using an ethyl acetate/hexanes gradient to afford 3.5mg of product. ES MS (+) m/z 378

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-chlorotoluene, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/70760; (2007); A2;,
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Electric Literature of 50638-47-6, 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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a magnetically stirring solution of 4-bromo-2-chloroanisole (0.50 g, 2.61 mmol) and 1- CYCLOPENTYL-2-PROPEN-1-OL (1.5 eq, 0.49 g, 3.88 mmol) in anhydrous N-methylpyrrolidinone (3.0 mL), under argon at room temperature, was added sodium bicarbonate (1.2 eq, 0.26 g, 3.10 mmol) followed by DICHLOROBIS (TRIPHENYLPHOSPHINE) PALLADIUM (II) (0.02 eq, 36.7 mg, 0.05 MMOL). The resulting mixture was heated to 140 C in an oil bath and maintained for 4 hours. The resulting dark reaction mixture was cooled to room temperature and poured into water (50 mL) and extracted with EtOAc (2 X 25 mL). The organics were washed with water (50 mL) and brine (50 mL) then dried over NA2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (1% through 10% EtOAc in Hexanes) to yield the intermediate ketone as a slightly yellow oil (0.49 g, 79%).

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

Reference:
Patent; PFIZER INC.; WO2004/74270; (2004); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics