Tag: M.W=200-300

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. 21865-50-9, name is 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, A new synthetic method of this compound is introduced below., Recommanded Product: 21865-50-9

To a suspension of 39 (0.75 g, 3.0 mmol) in acetic acid (3 ml) is added acetyl chloride (0.21 ml, 3.0 mmol). The mixture is heated to reflux, resulting in a clear solution. After 2 hours, the reaction solution is cooled to room temperature (rt). A solid is precipitated out. The solid 48 is filtered and washed with hexanes (2 x), 0.24 g, 27%

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; PTC THERAPEUTICS, INC.; WO2006/58088; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5153-40-2, 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. 5153-40-2 name is 1-Bromo-2,3,4,5,6-pentamethylbenzene, 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.

The synthesis of salicylaldimine 13 was accomplished in five steps (FIG. 21). Negishi cross-coupling of 1 and pentamethylbromobenzene[Ref 54] afforded biphenyl species 9. Subsequent steps are similar to the synthesis of ligands 7-s and 7-a. Bromination, followed by lithium-halogen exchange and DMF treatment installed the formyl moiety to give 11. Deprotection of the ether group and condensation with 2,6-diisopropyl aniline provided 13 in 14% overall yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,3,4,5,6-pentamethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; RADLAUER, Madalyn; WIENSCH, Joshua D.; BUCKLEY, Aya K.; AGAPIE, Theodor; US2013/66029; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 69902-83-6, name is 1-Bromo-2-methyl-3-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Formula: C8H6BrF3

Step 1 : A mixture of 1-bromo-2-methyl-3-(trifluoromethyl)benzene (100 mu, 0.64 mmol), 4,4,5,5-tetramethyl-2-(tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,3,2- dioxaborolane (327 mg, 1.29 mmol), PdCI2dppf DCM (26 mg, 0.030 mmol) and potassium acetate (158 mg, 1.61 mmol) in 1 ,4-dioxane (5 mL) was heated in a sealed tube at 80C overnight. The mixture was run through a plug of silica (EtOAc), concentrated and purified by preparative HPLC to give 4,4,5,5- tetramethyl-2-[2-methyl-3-(trifluoromethyl)phenyl]-1 ,3,2-dioxaborolane.

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; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

320-29-6, name is 4-Bromo-1,2-bis(trifluoromethyl)benzene, 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. category: bromides-buliding-blocks

Sodium Hydride (60% oil suspension, 5 mmol, 200 mg) is triturated with hexane and suspended in N,N-dimethylformamide (4 mL). 1,2,3,9-Tetrahydro-carbazol-4-one (2.5 mmol, 462 mg) is added to the water-cooled suspension. After 5 minutes, 5-bromo-2-trifluorobenzotrifluoride (5 mmol, 0.71 g) is added. The reaction is stirred at 85 degrees Celsius for 3.5 h. The reaction mixture is allowed to cool and is extracted into ethyl acetate (200 mL) and is washed with water (50 mL). The organic phase is dried over magnesium sulfate. Filtration, followed by concentration, and silica gel chromatography affords the desired 9-(4-Bromo-2-trifluoromethyl-phenyl)-1,2,3,9-tetrahydro-carbazol-4-one as a brown foam (0.74 g, 73%).

The synthetic route of 320-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Serenex, Inc.; US2007/185184; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 41825-73-4, name is 2-Bromo-4,6-dimethylaniline, A new synthetic method of this compound is introduced below., SDS of cas: 41825-73-4

N-(2-Bromo-4,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilanamine Under an argon atmosphere, to a solution of 14.8 g (74.2 mmol) of 2-bromo-4,6-dimethylaniline in 200 ml of THF, 29.7 ml of 2.5 M (74.2 mmol) nBuLi in hexanes was added at -80 C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 18.0 g (74.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 100 ml of THF. The resulting mixture was stirred overnight at ambient temperature, and then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 168-172 C./0.2 mm Hg. The product crystallizes slowly at ambient temperature. Yield 16.5 g (55%). Anal. calc. for C19H24BrNSSi: C, 56.14; H, 5.95. Found: C, 56.28; H, 6.09. 1H NMR (CDCl3): delta 7.20 (d, J=4.9 Hz, 1H, 3-H in cyclopenta[b]thiophene), 7.18 (m, 1H, 3-H in phenyl), 6.97 (d, J=4.9 Hz, 1H, 2-H in cyclopenta[b]thiophene), 6.85 (m, 1H, 5-H in phenyl), 3.59 (br.s, 1H, 6-H in cyclopenta[b]thiophene, 2.92 (br.s, 1H, NH), 2.21 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.13 (s, 3H, 4-Me in cyclopenta[b]thiophene), 2.10 (s, 3H, 5-Me in cyclopenta[b]thiophene), 0.14 (s, 3H, SiMeMe’), 0.06 (s, 3H, SiMeMe’). 13C NMR (CDCl3): delta 152.2, 140.7, 140.0, 139.2, 132.6, 132.4, 131.2, 131.1, 130.0, 126.2, 119.9, 118.0, 49.2, 20.8, 20.6, 15.4, 12.1, -1.8, -2.1.N-(2-Bromo-4,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilanamine Under and argon atmosphere, to a solution of 14.8 g (74.2 mmol) of 2-bromo-4,6-dimethylaniline in 200 ml of THF, 29.7 ml of 2.5 M (74.2 mmol) nBuLi in hexanes was added at -80 C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise for ca. 1 hour while vigorously stirring to a solution of 18.0 g (74.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 100 ml of THF. The resulting mixture was stirred overnight at ambient temperature, then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 168-172 C./0.2 mm Hg. The product crystallizes slowly at ambient temperature. Yield 16.5 g (55%). Anal. calc. for C19H24BrNSSi: C, 56.14; H, 5.95. Found: C, 56.28; H, 6.09. 1H NMR (CDCl3): delta 7.20 (d, J=4.9 Hz, 1H, 3-H in cyclopenta[b]thiophene), 7.18 (m, 1H, 3-H in phenyl), 6.97 (d, J=4.9 Hz, 1H, 2-H in cyclopenta[b]thiophene), 6.85 (m, 1H, 5-H in phenyl), 3.59 (br.s, 1H, 6-H in cyclopenta[b]thiophene, 2.92 (br.s, 1H, NH), 2.21 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.13 (s, 3H, 4-Me in cyclopenta[b]thiophene), 2.10 (s, 3H, 5-Me in cyclopenta[b]thiophene), 0.14 (s, 3H, SiMeMe’), 0.06 (s, 3H, SiMeMe’). 13C NMR (CDCl3): delta 152.2, 140.7, 140.0, 139.2, 132.6, 132.4, 131.2, 131.1, 130.0, 126.2, 119.9, 118.0, 49.2, 20.8, 20.6, 15.4, 12.1, -1.8, -2.1.

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:
Patent; Voskoboynikov, Alexander Z.; Ryabov, Alexey N.; Nikulin, Mikhail V.; Lygin, Alexander V.; Uborsky, Dmitry V.; Coker, Catalina L.; Canich, Jo Ann M.; US2007/135623; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 392-83-6, name is 2-Bromobenzotrifluoride, A new synthetic method of this compound is introduced below., Recommanded Product: 392-83-6

General procedure: A test tube equipped with a magnetic stir bar was charged with an aryl halide(aryl halide, 1 mmol),CuSO4.5H2O(12.5 mg, 0.05 mmol),KOH (280 mg, 5 mmol) orCs2CO3 (1.62 g, 5 mmol), DMSO (2 mL), and water (0.2 mL; water was not used in case of using Cs2CO3 as base).After flushing with argon, 1,2-ethanedithiol (0.18 mL, 2 mmol) was added.The mixture was heated in a preheated oil bath for 20 hours90 C or 110 C bath which is pre-heated with agitation.After cooling to ambient temperature, the reaction mixture was distributed in aqueous HCl (5%) and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc / n-Hexane) to give the aryl thiol (see Table 2 below).

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; SUNGSHIN WOMEN`S UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; CHAE, Junghyun; Liu, Ya jun; KIM, Ji hye; (18 pag.)KR2017/76524; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 21865-50-9,Some common heterocyclic compound, 21865-50-9, name is 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, molecular formula is C12H12BrN, 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 3. 6-Bromo-9-ethyl-2,3,4,9-tetrahydro-1H-carbazole; A 500-mL round-bottomed flask was charged with 3-bromo-6,7,8,9-tetrahydro-5H-carbazole (5 g, 20.08 mmol, 1.00 equiv) in N,N-dimethylformamide (270 mL). To this solution was added sodium hydride (1.2 g, 30.00 mmol, 1.50 equiv, 60%) in several batches at -10 C., followed by addition of iodoethane (6.26 g, 40.13 mmol, 2.00 equiv) as a solution in N,N-dimethylformamide (30 mL) drop wise -10 C. The resulting mixture was stirred at room temperature for 30 minutes. The reaction progress was monitored by TLC (EtOAc:PE=1:1). Upon completion, the reaction was then quenched by the addition of water/ice (120 mL). Then, the mixture was extracted with ethyl acetate (4×80 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The residue was purified by a silica gel column chromatography eluted with ethyl acetate/petroleum ether (1/20) affording 3-bromo-9-ethyl-6,7,8,9-tetrahydro-5H-carbazole as brown oil (5 g, 90%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, its application will become more common.

Reference:
Patent; Kalypsys, Inc; US8080566; (2011); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 32863-30-2, name is 4-(Bromomethyl)benzo[c][1,2,5]oxadiazole, 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. Formula: C7H5BrN2O

Compound 9-2 (44.5 mg, 0.1 mmol) and 4-(bromomethyl)benzo[c][1,2,5]oxadiazole 14-1 (32 mg, 0.15 mmol) were dissolved in dry DMF Add cesium carbonate (65.2mg, 0.2mmol) and stir at room temperature for about two hours. The reaction is complete. the reaction solution was extracted with water and ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. PE: EA = 5: 1 to give 20 mg of compound 14-2.

The synthetic route of 4-(Bromomethyl)benzo[c][1,2,5]oxadiazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Geng Meiyu; Song Zilan; Ai Jing; Gu Wangting; Liu Bo; Ding Jian; (28 pag.)CN110240587; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 875664-41-8, 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. 875664-41-8 name is 3-Bromo-4,5-difluoroaniline, 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.

1 -methyl-4-[(3 -methyloxetan-3 -yl)sulfamoyl]pyrrole-2-carboxylic acid (200 mg, 0.73 mmol) was dissolved in N,N-dimethylformamide (2 mL). HATU (0.35 g, 0.91 mmol) was added followed by diisopropylethylamine (0.38 mL, 2.19 mmol). The resulting mixture was stirred for 30 minutes at room temperature. Then, 4-fluoro-3,5-dimethylaniline (0.2 g, 1.46 mmol) was added. The resulting mixture was stirred for 24 hours and next poured onto 10 mL of ice. The mixture was extracted using 2-Me-THF (3 x 10 mL). The combined organics were washed withbrine, dried on Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0:100). The desired fractions were concentrated in vacuo and dried in a vacuum oven at 55C for24 hours yielding compound 80 (130 mg):Compound 100 to 105 were prepared similarly as described for compound 80, using 1-methyl-4-[[(1 S)-2,2,2-trifluoro- 1 -methyl-ethyl]sulfamoyl]pyrrole-2-carboxylic acid instead of 1 -methyl-4-[(3 -methyloxetan-3 -yl)sulfamoyl]pyrrole-2-carboxylic acid and the corresponding aniline instead of 4-fluoro-3 ,5 -dimethylaniline. After addition of the aniline, the mixture was stirred at 50C forhours instead of 24 hours at room temperature.Crude compound 100 was purified by silica gel chromatography heptane-EtOAc 100/0 to 0/100. The product was crystallized from diisopropylether (15 mL)/iPrOH (3.5 mL). The product wasfiltered off, washed with diisopropylether (3x), and dried at 50C in vacuo, resulting in compound 100 (251 mg). MethodA; Rt: 1.98 mi mlz: 489.8 (M-H) Exactmass: 491.0. ?HNMR (400 MHz, DMSO-d6) oe ppm 1.08 (d, J=6.8 Hz, 3 H), 3.84 – 4.00 (m, 4 H), 7.36 (d, J=2.0Hz, 1 H), 7.66 (d, J=1.8 Hz, 1 H), 7.80 – 7.93 (m, 2 H), 8.20 (br. s., 1 H), 10.31 (br. s., 1 H).?9FNMR (377 MHz, DMSO-d6) oe ppm -138.51 –138.34 (m, 1 F), -133.99 –133.81 (m, 1 F), -76.07 (d, J=7.9 Hz, 3 F). Differential scanning calorimetry: From 30 to 300 C at 10C/mm:peak at 199.0 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4,5-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 376646-62-7, name is (4-Bromo-2-methylphenyl)methanamine, 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. Safety of (4-Bromo-2-methylphenyl)methanamine

[0115] To a solution of (4-bromo-2-methylphenyl)methanamine (1.2 g, 6 mmol) in DCM (30 mL) were added TEA (1.82 g, 18 mmol) and Boc20 (1.43 g, 6.6 mmol). The mixture was stirred at room temperature for 1 h. After diluted with water (50 mL), the mixture was extracted with DCM (50 mL x2). The combined organics were washed with brine (50 mL), dried (Na2S04), filtered and concentrated to give crude title product (1.7 g, yield 95%) as a white solid, which was used directly in the next step without further purification. ESI-MS (M+H)+: 300.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 376646-62-7, its application will become more common.

Reference:
Patent; BIOGEN MA INC.; MACPHEE, J. Michael; CHEN, Robbie; FERGUSON, Steven; FRANKLIN, Lloyd; MACK, Tamera, L.; (78 pag.)WO2016/201271; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary