Tag: M.W=200-300

Electric Literature of 698-00-0,Some common heterocyclic compound, 698-00-0, name is 2-Bromo-N,N-dimethylaniline, molecular formula is C8H10BrN, 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: Under air, 1 (0.2 mmol), NH4I (0.8 mmol), 70% TBHP in water (2.4 mmol) and DMSO (0.5 mL) were added to a 10 mL Schlenk tube sealed with a Teflon lined cap. The reaction mixture was stirred at 90 C for 4 h in an oil bath. Upon completion, the reaction mixture was left to cool to room temperature and slowly quenched with anhydrous sodium sulfite. The reaction mixture was then diluted with ethyl acetate (5 mL) and then washed with water (5 × 5 mL). The aqueous layer was extracted with EtOAc (3 × 5 mL). The combined organic layers were dried over Na2SO4. The filtrate was concentrated and the crude product was purified by column chromatography on silica gel with petroleum ether (60-90 C)/ethyl acetate eluent. Characterisation data are consistent with literature data.

The synthetic route of 698-00-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shao, Ying; Zheng, Hao; Wu, Zhuhong; Huang, Lei; Tong, Jingjing; Wu, Ming; Sun, Xiaoqiang; Journal of Chemical Research; vol. 41; 9; (2017); p. 504 – 508;,
Bromide – Wikipedia,
bromide – Wiktionary

698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, 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: 1-(2-Bromophenyl)-N-methylmethanamine

A mixture of compound 1A (4.30 g), [N-Boc-glycine] (3.01 g, 17.1 mmol), EDC (3.28 g, 17.1 mmol), and HOAt (2.34 g, 17.1 mmol) in DCM (50 ml) was stirred at rt overnight. The reaction was quenched with the addition of sat’d NaHCO3 solution. The organic layer was separated, washed with brine, dried MgSO4), and concentrated to give the crude product which was purified by flash chromatography (10-20% EtOAc/ hexane) to give compound 1B (3.35 g) as a colorless film.

The synthetic route of 698-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2004/788; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 454-79-5, 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. 454-79-5 name is 2-Bromo-5-(trifluoromethyl)aniline, 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.

A resealable tube was charged with 2-bromo-5- (trifluoromethyl)aniline (1.00 g, 4.16 mmol), 1- dimethylamino-2-propyne (0.520 g, 6.20 mmol), PdCl2(PPh3J2 (0.15 g, 0.21 mmol), copper iodide (0.80 mg, 0.42 mmol), diisopropylethylamine (1.0 mL) and acetonitrile (3.0 mL) . The system was purged with argon, the tube sealed and the mixture stirred at room temperature for 20 h. The reaction EPO mixture was filtered through celite and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0-10% methanol-dichloromethane) to afford 2- (3-dimethylamino-l-propynyl) -5- (trifluoromethyl)aniline as a brown oil. MS m/z = 243 [M+H]+. CaIc’d for C12H13F3N2: 242.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; WO2006/44823; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 16518-62-0,Some common heterocyclic compound, 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, molecular formula is C8H10BrN, 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 mixture ofpalladium(ll) acetate (3 mg, 5 molpercent), 2-dicyciohexylphosphino-2′-(A/,A/-dimethylamino)biphenyl (10 mg, 5 molpercent) and lithium bis(trimethylsilyl)amide(0.55 rnl_, 0.55 mmol, 1.1 equiv, 1.0 M solution in tetrahydrofuran) in toluene(0.5 ml) under nitrogen at-10 °C, was added a solution of 3-[5-(3,4-dichloro-10 phenyl)-1 -(2,4-dichloro-phenyl)-1 H-pyrazol-3-yl]-propionic acid tert-butyl ester(243 mg, 0.50 mmol, 1.0 equiv) in toluene (1.0 mL). This mixture was stirred at-10 °C for 10 min, then (3-bromo-phenyl)-dirnethyl-arnine (42 mg, 0.21 mmol,0.45 equiv) in toluene (0.5 ml) was added. The resulting solution was allowedto warm to room temperature then was heated to 80 °C for 3 h. The reaction15 mixture was cooled to room temperature, and the reaction was quenched withsatd aq ammonium chloride (1.0 ml). Water (10.0 ml) was added, and theresulting mixture was extracted with diethyl ether (2×10 ml). The combinedextracts were washed with brine (10 ml), dried (Na2SC>4), and concentratedunder reduced pressure. The crude material was purified by reversed-phase20 HPLC to afford the desired aryl acetic acid ester (20 mg, 16percent). MS (ESI):mass calculated for CaohbCUNaC^, 603.10; m/z found, 604.1 [M+H]+.

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-N,N-dimethylaniline, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/5393; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, molecular formula is C4H3BrF4, 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. Application In Synthesis of 4-Bromo-3,3,4,4-tetrafluorobut-1-ene

General procedure: In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar and reflux condenser, was added ethyl 2-iodobenzoate (3j, 0.14 g 0.50 mmol), Cu2O (0.060 g, 0.42 mmol), and a DMF solution of 2-Zn (0.65 M, 1.54 mL, 1.0 mmol), and the mixture was stirred at 100 C for 24 h. After being cooled to room temperature, the resulting solution was subjected to a short pad of silica gel using hexanes as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography to provide the corresponding compound 4j (0.13 g, 0.48 mmol) in 96% yield as an yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18599-22-9, its application will become more common.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, belongs to bromides-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 327-52-6, Quality Control of 1-Bromo-2,4,5-trifluorobenzene

Into a 100 mL three-necked flask were added 4.62 g 1-bromo-2,4,5-trifluorobenzene (0.022 mol) and anhydrous tetrahydrofuran (50 mL). The resulting mixture was cooled to -20 C. The solution of isopropylmagnesium bromide (22 mmol) in tetrahydrofuran (22 ml, 1M THF) was slowly added dropwise under nitrogen. After the addition was complete, the reactants were maintained at -20 C. for later use. Cuprous bromide-dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. The resulting mixture was cooled to -5 C. The Grignard reagent as described above was slowly added dropwise under nitrogen. After 15 min, a solution of the aziridine compound as shown in the above reaction formula (4.16 g, 0.015 mol) in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammonia chloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate. The separated water layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together and further washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followed by filtration and concentration to obtain a crude product, which was further treated by column chromatography to obtain a compound (4.08 g, 0.0116 mol, yield 77%). 1H NMR (400 MHz, CDCl3) delta7.537.22 (m, 10H), 7.05 (t, J=10.5 Hz, 1H), 6.93 (t, J=10.7 Hz, 1H), 5.12 (d, J=12.6 Hz, 1H), 3.973.85 (m, 1H), 3.82 (d, J=6.2 Hz, 1H), 3.773.55 (m, 1H), 3.62 (s, 2H), 3.51 (s, 2H), 2.82 (s, 2H), 1.871.68 (m, 1H), 1.631.48 (m, 1H). Ms (M++1): 400.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,4,5-trifluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; ZHEJIANG HISOAR PHARMACEUTICAL CO., LTD.; Pan, Xianhua; Li, Weijin; Zhang, Qunhui; Ruan, Libo; Yu, Wansheng; Deng, Fei; Ma, Tianhua; Huang, Mingwang; He, Minhuan; US2013/281695; (2013); 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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H2Br2F2

The compound 2,5-difluoro-1,4-dibromobenzene (2 g, 7.40 mmol) was sequentially added to a 100 mL single-necked flask, (4.7 g, 18.52 mmol), potassium acetate (4 g, 44.40 mmol), Pd(dppf)Cl2 (210 mg, 0.287 mmol) and 1,4-dioxane (25 mL) The temperature was raised to 80 under reflux for 24h. Stop the reaction and cool, the reaction solution was washed with saturated brine 4 times, extracted with DCM twice, the combined organic phase, Dried over anhydrous MgSO4 overnight, filtered and the organic solvent was spun off. The crude product was extracted with PE-DCM (v / v, 2/1) as eluent, and then recrystallized from n-hexane to give 2 g of white needle-like crystals, Yield: 74.1%

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 327-51-5.

Reference:
Patent; Changzhou University; Liu Yu; Liu Yajun; Zhu Weiguo; Wang Yafei; (26 pag.)CN107400147; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 133739-70-5, A common heterocyclic compound, 133739-70-5, name is 1-Bromo-2,3,5-trifluorobenzene, molecular formula is C6H2BrF3, 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 mixture of 17.28 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(prop-2-ynyl)-piperidine-3-carboxylate in 173 cm3 of triethylamine is stirred for 5 minutes under an inert atmosphere at a temperature in the region of 20 C. 4.05 g of tetrakis(triphenylphosphine)palladium, 0.834 g of cuprous iodide and 7.9 g of 1-bromo-2,3,5-trifluorobenzene are added.The mixture is stirred for 2 hours at a temperature in the region of 80 C. After cooling to approximately 20 C., 150 cm3 of ethyl acetate and 150 cm3 of water are added to the reaction mixture, which is then separated after settling out.The aqueous phase is extracted with 3 times 150 cm3 of ethyl acetate.The organic phases are pooled, washed with 5 times 150 cm3 of water, dried over sodium sulfate, filtered, and concentrated under reduced pressure (5 KPa) at a temperature in the region of 40 C. The residue obtained is purified by chromatography under a nitrogen pressure of 50 KPa, on a column of silica gel (particle size 20-45mu; diameter 7 cm; 600 g), eluding with pure ethyl acetate and collecting first a fraction of 2.5 1, and then fractions of 250 cm3.Fractions 2 to 29 are pooled and then concentrated as above. 18.4 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-piperidine-3-carboxylate, in the form of a yellow oil, are obtained. [0293] 1H NMR spectrum (400 MHz, (CD3)2SO d6, delta in ppm): from 1.55 to 1.95 (mt: 5H); 2.39 (mt: 1H); 2.58 (broad d, J=10 Hz: 1H); 2.68 (mt: 1H); 2.82 (mt: 1H); 2.91 (mt: 1H); 3.09 (mt: 1H); 3.23 (mt: 1H); 3.58 (s: 3H); 3.61 (s: 2H); 3.88 (s: 3H); 7.31 (mt: 1H); 7.49 (dd, J=9 and 2.5 Hz: 1H); from 7.55 to 7.65 (mt: 1H); 7.73 (d, J=2.5 Hz: H); 7.92 (d, J=4.5 Hz: 1H); 8.02 (d, J=9 Hz: 1H); 8.89 (d, J=4.5 Hz: 1H).

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; Bacque, Eric; Bigot, Antony; Ahmad, Youssef Ei; Malleron, Jean-Luc; Mignani, Serge; Ronan, Baptiste; Tabart, Michel; Viviani, Fabrice; US2004/87619; (2004); 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. 328-70-1, name is 1-Bromo-3,5-bis(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-3,5-bis(trifluoromethyl)benzene

10 g of 3,5-bis(trifluoromethyl)bromobenzene are mixed with 11 ml of cyclohexyldimethylamine and 30 ml of dimethylacetamide and degassed. 38 mg of palladium acetate and 152 mg of di(tert-butyl)phenylphosphine are dissolved in 5 ml of dimethylacetamide and added to the mixture. The mixture is transferred to an autoclave and 30 bar of ethylene are injected. The mixture is then heated to 110 C. and stirred at this temperature for 3 hours. At the end of the reaction, the mixture is cooled and the pressure released. Subsequently, 8.3 g of 1,5-dimethyl-3-trifluoromethyl-1H-pyrazole are added to the reaction mixture and the mixture is heated to 130 C. for 12 h. Afterwards, the mixture is cooled, added to water and worked up with toluene. Yield over the two steps: 10.5 g (76%) of slightly brownish solid.

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 328-70-1.

Reference:
Patent; Ebenbeck, Wolfgang; Rampf, Florian; Marhold, Albrecht; US2004/142820; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 54962-75-3,Some common heterocyclic compound, 54962-75-3, name is 3-Bromo-5-(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.

To a solution of 3-amino-5-bromo-benzotrifluoride (1.0 g) in degassed (argon) tetrahydrofuran (2 mL) is added bis-(tri-o-tolylphosphino)palladium (0.15 g), a solution of dimethylamine in tetra-hydrofuran (2M, 4.2 mL), and a solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M, 10.4 mL). The reaction mixture is heated in a sealed vessel to 100C for approximately 2.5 hours to complete the reaction. The mixture is then cooled to room temperature, quenched by addition of water, and diluted with ethyl acetate. The product is extracted three times into 5% aqueous hydrochloric acid, and pooled acidic extracts are then basified with cooling by addition of 5N aqueous sodium hydroxide. This basic solution is then extracted with ethyl acetate, and these pooled organic extracts are washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. The resulting residue is chromatographed over silica gel (20-30% ethyl acetate in hexanes is used as the eluant) to provide the desired product as a slightly tinted solid.

The synthetic route of 54962-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; EP1137645; (2004); B1;,
Bromide – Wikipedia,
bromide – Wiktionary