Tag: M.W=200-300

Related Products of 138526-69-9, These common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, 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.

Argon gas protection 1000ml three-necked bottle, add cyclobutene benzoic acid 60g,77 g of 3,4,5-trifluorobromobenzene was added, and 5 g of tetrabutylammonium bromide was added.188 g of absolute ethanol was added, stirred until fully dissolved, and the temperature was raised to 40 C, and 0.6 g of a palladium chloride catalyst was added.Continue to heat up to 68 ~ 72 C weak reflux,Temperature control 68 ~ 72 C drop added Sodium carbonate 100g / water 200g solution,After the dropwise addition, the reaction was kept at this temperature for 4 h, the reaction was stopped, 200 g of toluene was added, and 200 g of water was added.Stir for 2h, separate the liquid, wash to neutral, dry, filter, and concentrate to obtain the product.GC analysis content >95%, yield >98%.

The synthetic route of 138526-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Shenghua Science And Technology Chuangyeyuan Co., Ltd.; Wu Shengxi; Liu Yuyang; Wang Dexian; Du Kaichang; Gao Genhua; (10 pag.)CN108178720; (2018); A;,
Bromide – Wikipedia,
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142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, belongs to bromides-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. name: 4-Bromo-2-fluorobenzotrifluoride

step 2: To a solution of 4-bromo-2-fluoro-l-(trifluoromethyl)benzene (4.854 g, 19.98 mmol) and ether (50 mL) cooled to -78 C was added butyl lithium (7.990 mL, 19.98 mmol) slowly over 10 min. The reaction was transferred via cannula to a solution of 74 (4.30 g, 16.65 mmol) in THF (50 mL) cooled to -78 C. The reaction was stirred for 10 min after all aryl lithium was added. The reaction was quenched with water and extracted with DCM. The organic layer was concentrated and the crude product purified by Si02 chromatography eluting with an EtOAc/hexane (1 to 5% EtOAc). A close running impurity was not removed by this purification. A Si02 column was run eluting with an Et20/hexane gradient (1 to 3% Et20). The impurity was still present and the compound was finally purified on a SP4 reverse phase column chromatography eluting with MeCN/water gradient (65 to 100% MeCN) to afford 2.105 g (33.2%) of (R)-tert-butyl 2-(3-fluoro-4-(trifluoromethyl)benzoyl)-pyrrolidine-l-carboxylate (76).

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James F.; CHEN, Huifen; CHICARELLI, Mark Joseph; DEMEESE, Jason; GARREY, Rustam; GAUDINO, John J.; KAUS, Robert J.; KOLAKOWSKI, Gabrielle R.; MARLOW, Allison L.; MOHR, Peter J.; REN, Li; SCHWARZ, Jacob; SIEDEM, Christopher S.; THOMAS, Allen A.; WALLACE, Eli; WENGLOWSKY, Steven Mark; WO2012/118850; (2012); A1;,
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Electric Literature of 50548-45-3, A common heterocyclic compound, 50548-45-3, name is 1-Bromodibenzo[b,d]furan, molecular formula is C12H7BrO, 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 500 ml round bottom flask in a nitrogen atmosphereCompound 1-Bromobenzofuran (10.0 g, 40.65 mmol),N – ([1,1′-biphenyl] -4-yl) – [1,1 ‘: 4′, 1 ” – terphenyl]-4-amine ((N – ([1,1’-biphenyl] -4-yl) – [1,1 ‘: 4’, 1 ” – terphenyl]-4-amine)(17.75 g, 44.72 mmol)Xylene(Xylene)After completely dissolved Sodium tert-butoxide(sodium tert-butoxide)(5.08 g, 52.85 mol) was added,Bis (tri-tert-butylphosphine) palladium (0)(Bis (tri-tert-butylphosphine) palladium (0)) (0.21 g, 0.41 mmol)And the mixture was heated and stirred for 6 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (250 ml) to obtain Compound (4) (18.89 g, yield: 82%)

The synthetic route of 50548-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG CHEM, LTD.; KIM, Jin Joo; HONG, Sung gil; CHA, Yong bum; (27 pag.)KR2017/94665; (2017); A;,
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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 6274-57-3 as follows. Product Details of 6274-57-3

. Example 10. Synthesis of tributyl[{(4-dimethylamino)methyl}phenyl]stannane (S8)”BuLi To (4-bromobenzyl)dimethylamine (2.14 g, 10.0 mmol, 1.00 equiv) in Et2O (25 niL) at 23 0C was added “BuLi (2.4 M in hexane, 4.17 niL, 10 mmol, 1.0 equiv). The reaction mixture was warmed to 23 0C and stirred for 2.0 hr before the addition of “Bu3SnCl (3.25 g, 10.0 mmol, 1.00 equiv) at -78 0C. After stirring for 1.0 hr at 23 0C, the reaction mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with hexanes/EtOAc 1:1 (v/v) to afford 3.35 g of the title compound as a colorless oil (79% yield). R/= 0.20 (hexanes/EtOAc 1:1 (v/v)). NMR Spectroscopy: 1H NMR (500 MHz, CDCl3, 23 0C, delta): 7.42 (d, / = 6.5 Hz, 2H), 7.27 (d, / = 6.5 Hz, 2H), 3.41 (s, 2H), 2.26 (s,6H), 1.64-1.48 (m, 6H), 1.40-1.30 (m, 6H), 1.15-0.99 (m, 6H), 0.90 (t, / = 6.0 Hz, 9H). 13C NMR (100 MHz, CDCl3, 23 0C, delta): 140.30, 138.40, 136.36, 128.72, 64.40, 45.36, 29.07, 27.35, 13.64, 9.52. Mass Spectrometry: HRMS-FIA (m/z): Calcd for [M + H]+, 426.21772. Found, 426.21651.

According to the analysis of related databases, 6274-57-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; RITTER, Tobias; FURUYA, Takeru; TANG, Pingping; WO2010/59943; (2010); A2;,
Bromide – Wikipedia,
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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. 1074-24-4, name is 1,4-Dibromo-2,5-dimethylbenzene, A new synthetic method of this compound is introduced below., Formula: C8H8Br2

Under a nitrogen stream 2,5-dibromo-p-xylene (25.0 g, 94.71 mmol) is added to diethylether (350 mL), the temperature is lowered to -78 ¡ã C, and then 2.5 M n-BuLi (31.5 g, 113.6 mmol) is added slowly. After the temperature was raised to room temperature, the mixture was stirred for 1 hour, and then DMF (8.3 g, 113.65 mmol) was added slowly at -78 ¡ã C, followed by stirring at room temperature for 12 hours. To terminate the reaction, the reaction mixture is poured into water and extracted with diethylether. The organic layer is washed with MgSO4 to remove water and the solvent is removed. A white solid was obtained using a silica column (Hexane). (15.6 g, 71percent). 1H NMR (300 MHz, CDCl3, delta): 10.12(s, 1H), 7.38(s, 1H), 7.30(s, 1H), 2.35(s, 6H).

The synthetic route of 1074-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Institute of Industrial Technology; Lee, Young Chul; Kim, Myung Jun; Kim, Baek Jin; Hwang, Suk Ho; Jung, Sung Wook; Kim, Chang Joo; (13 pag.)KR101610235; (2016); B1;,
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Application of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

[000849j To a stirred solution of compound 3 (1 g, 1 eq) in POC13 (2 mL), cyclopropane carboxylic acid (0.5 mL) were added. The resulting reaction mixture was heated at 120 C for 3h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate (3 X 20 mL). Combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 20% EtOAc-hexane to afford the title compound 4. LCMS (mlz): 250.95 (M + 1).

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Bromide – Wikipedia,
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Electric Literature of 138526-69-9, The chemical industry reduces the impact on the environment during synthesis 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, I believe this compound will play a more active role in future production and life.

Intermediate T(l)(lS,2R)-2-(3,4,5-Trifluorophenyl)cyclopentanolTo a suspension of magnesium (2.88 g, 118 mmol) in THF (1 10 mL) was slowly added 5-bromo-l,2,3-trifluorobenzene (25 g, 118 mmol). After the addition, the reaction mixture was heated at reflux for 2 h. To this reaction mixture, copper (I) iodide (1.506 g, 7.91 mmol) and 6-oxabicyclo[3.1.0]hexane (9.93 g, 118 mmol) dissolved in THF (20 mL) were added dropwise. The reaction mixture warmed upon the addition of the epoxide. The reaction was stirred at rt for 2 h at rt. The reaction mixture was quenched by the addition of a solution of ammonium chloride. Ether was added and the organic layer was collected, dried ( a2S04) and concentrated. The crude product was purified by column chromatography on silica gel to give (l S,2R)-2-(3,4,5-trifluorophenyl)cyclopentanol (20.2 g, 93 mmol, 79 % yield).? NMR (500 MHz, CDC13) delta ppm 6.79 – 7.02 (2H, m), 4.10 – 4.21 (1H, m), 2.75 – 2.91 (1H, m), 2.08 – 2.24 (2H, m), 1.75 – 1.93 (2H, m), 1.50 – 1.75 (2H, m).

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-3,4,5-trifluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, Lorin A., III.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2012/103297; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 393-36-2,Some common heterocyclic compound, 393-36-2, name is 4-Bromo-3-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.

4-Bromo-3-(trifluoromethyl)aniline was converted into 4-bromo-3-(trifluoromethyl)phenyl isocyanate according to Method B1. According to Method C1a, 4-bromo-3-(trifluoromethyl)phenyl isocyanate was reacted with 3-(-2-(N-methylcarbamoyl)-4-pyridyloxy)aniline to afford the urea. Entry 90: According to Method A2, Step 4, 5-amino-2-methylphenol was reacted with 4-chloro-N-methyl-2-pyridinecarboxamide, which had been synthesised according to Method A2, Step 3b, to give 3-(2-(N-methylcarbamoyl)-4-pyridyloxy)-4-methylaniline.

The synthetic route of 393-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Riedl, Bernd; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Monahan, Mary-Katherine; Natero, Reina; Renick, Joel; Sibley, Robert N.; US2001/11135; (2001); A1;; ; Patent; BAYER CORPORATION; US2002/165394; (2002); A1;; ; Patent; BAYER CORPORATION; US2003/181442; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 100189-84-2, name is 2,5-Dibromo-1,3-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 2,5-Dibromo-1,3-dimethylbenzene

Step 2: synthesis of (E)-3-(4-bromo-3,5-dimethylphenyl)acrylonitrile (compound lb) Compound lb [0250] To a solution of 2,5-dibromo-l ,3-dimethylbenzene (2640 mg, 10 mmol, Oakwood Products, Inc. – 018507) in anhydrous acetonitrile (25 mL) was added palladium(II) acetate (1 12 mg, 0.5 mmol), acrylonitrile (531 mg, 10 mmol), tri(o-tolyl)phosphine (131 mg, 0.5 mmol) and triethylamine (4 mL, 30 mmol) then the mixture was purged with argon and heated at 1 10 C for 2 hours. The reaction mixture was filtered through Celite and the filter pad was washed with tetrahydrofuran (10 mL). The filtrate was evaporated then re-dissolved with ethyl acetate (50 mL). The solution was washed with water (50 mL). The water layer was back extracted with ethyl acetate (50 mL). The combined organics were washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude residue. This was subjected to silica gel chromatography (gradient from 0-20% ethyl acetate in wo-hexanes) to afford the crude product which was treated in sonic bath with hexane (10 mL) for 10 minutes. The product precipitated out of solution and was collected by filtration. The solids were washed with cold hexane to afford compound lb. NMR (400 MHz, CDC13) 6 7.25 (d, J= 16.6 Hz, 1H), 7.12 (s, 2H), 5.84 (d, J = 16.6 Hz, 1H), 2.42 (s, 6H). LCMS (m/z) no MS signal, Tr = 2.78 min (LCMS method 2).

According to the analysis of related databases, 100189-84-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE AS CR, V.V.I.; JANSA, Petr; SIMON, Tetr; LANSDON, Eric; HU, Yunfeng, Eric; BASZCZYNSKI, Ondrejj; DEJMEK, Milan; MACKMAN, Richard, L.; (185 pag.)WO2016/105564; (2016); A1;,
Bromide – Wikipedia,
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Application of 33070-32-5, These common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, 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.

Step 1: A mixture of 5-bromo-2,2-difluoro-1,3-benzodioxole (15.0 g, 63.6 mmol), ethyl cyanoacetate (14.4 g, 127 mmol) and Na3PO4 (31.2 g, 191 mmol) in toluene (180 mL) was degassed three times and back filled with N2. Then Pd(dba)2 (1.46 g, 2.54 mmol) and PtBu3 (10% w/w in hexane, 10.3 g, 5.08 mmol) were added. H20 (0.9 mL) was added and the mixture was degassed three times and back filled with N2. The mixture was heated at 90C for 18 hours. The mixture was diluted with EtOAc (200 mL) and filtered. The filtrate was washed with H20 (100 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated to give 17 g of crude ethyl 2-cyano-2-(2,2-difluorobenzo[d][1,3]dioxol-5- yl)acetate as a black oil, which was used directly for the next step.

Statistics shows that 5-Bromo-2,2-difluorobenzodioxole is playing an increasingly important role. we look forward to future research findings about 33070-32-5.

Reference:
Patent; N30 PHARMACEUTICALS, INC.; SUN, Xicheng; QIU, Jian; STOUT, Adam; WO2014/186704; (2014); A2;,
Bromide – Wikipedia,
bromide – Wiktionary