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. 40422-70-6, name is 1-Bromo-3-(2-bromoethyl)benzene, A new synthetic method of this compound is introduced below., Product Details of 40422-70-6

To a 100 mL three neck round bottomed flask under nitrogen atmosphere, (R)-2- isopropyl-3,6-dimethoxy -2,5- dihydropyrazine (4 g, 21.7 mmol) was dissolved in dry THF (28 mL) and cooled to -78 C. To this reaction mixture, 1.6 M solution of n-BuLi in hexanes (16.28 mL, 26 mmol) was added dropwise at -78 C and stirred at same temperature for 15 minutes. After 15 minutes, l-bromo-3- (2-bromoethyl)benzene (5.73 g, 21.7 mmol) in dry THF (13 mL) was added dropwise at -78 C and stirred at -78 C for 1 h followed by stirring at room temperature (rt) for 3 h. The reaction was monitored by TLC using ethyl acctatc hcxancs (0.3:9.7) as a mobile phase. After completion of the reaction, reaction mixture was quenched with saturated ammonium chloride solution (75 mL) and extracted using ethyl acetate (3 x 100 mL). Combined organic layer was dried over sodium sulphate and concentrated to give crude which was purified by flash column purification with 1-3 % ethyl acetate in hexanes to yield 3.3 g of (2S,5R)-2-(3-bromophenethyl)-5- isopropyl-3, 6-dimethoxy-2,5-dihydropyrazine (41.38% yield).

The synthetic route of 40422-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; LOU, Yan; OWENS, Timothy Duncan; BRAMELD, Kenneth Albert; GOLDSTEIN, David Michael; (171 pag.)WO2019/99576; (2019); 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. 627526-90-3, name is 1-Bromo-3-(difluoromethyl)-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H4BrF3

(B) To a solution of 1-bromo-3-(difluoromethyl)-5-fluorobenzene (8.6 g, 38.56 mmol, I eq) and DIPEA(13.44 ml, 77.12 mmol, 2 eq) in 1,4-dioxane (150 ml) was added PMB-SH (5.89 ml, 42.42 mmol, 1.1 eq).The mixture was degassed for 10 mm, and Xantphos (1.56 g, 2.69 mmol, 0.07 eq), followed by Pd2(dba)3 (1.0 g, 1.15 mmol, 0.03 eq) were added. The mixture was again degassed for 10 mm. The resulting RM was heated to 90 C and stirred for 2 h under Ar. The RM was filtered through celite and the filtrate concentrated to yield the crude product, which upon flash chromatography afforded 1 -bromo-3-(difluoro-methyl)-5-fluorobenzene (10 g, 87%).

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 627526-90-3.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 41825-73-4, 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. 41825-73-4 name is 2-Bromo-4,6-dimethylaniline, 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.

General procedure: 2-iodoaniline (0.5 mmol) or 2-bromoaniline (0.5 mmol), complex 1 (0.05mmol), K2CO3 (1 mmol), (n-Bu)4NBr (0.1 mmol) and water (10 mL) were added to a sealed tube. The reaction mixture was stirred at 120oC for 30 h, then cooled to room temperature and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the solvent was then removed under reduced pressure. The product was finally obtained by column chromatography on silica gel.

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

Reference:
Short Survey; Yu, Lintao; Zhou, Xiangge; Wu, Di; Xiang, Haifeng; Journal of Organometallic Chemistry; vol. 705; (2012); p. 75 – 78;,
Bromide – Wikipedia,
bromide – Wiktionary

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 875664-41-8 as follows. Quality Control of 3-Bromo-4,5-difluoroaniline

Compound 99 A mixture of 3-(N-isopropylsulfamoyl)benzoic acid (2.3 g, 9.615 mmol), 3-bromo-4,5- difluoroaniline (2 g, 9.615 mmol) and DIPEA (5 mL) in CH2CI2 (30 mL) was cooled to 0C and HATU (4.39 g, 1 1.538 mmol) was added. The mixture was stirred for 2 hours at 20C. The mixture was washed with IN HC1 (30 mL) and brine (30 mL) and dried over Na2S04. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 70/30) resulting in crude N-(3-bromo-4,5-difluorophenyl)-3-(N-isopropylsulfamoyl)- benzamide (4 g). A mixture of N-(3-bromo-4,5-difluorophenyl)-3-(N-isopropyl- sulfamoyl)benzamide (1 g, 2.308 mmol), methylboronic acid (1 g, 4.616 mmol), CS2CO3 (2.26 g, 6.924 mmol), 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (95 mg, 0.231 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.21 g, 0.231 mmol) in dioxane (15 mL) was heated by microwave irradiation for 40 minutes at 120C under N2 atmosphere. After cooling, the mixture was filtered through celite and the filtrate was evaporated to dryness. The obtained residue was purified by silca gel column chromatography (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 70/30) and further purified by preparative high performance liquid chromatography over reversed phase C-18 (eluent: CH3CN in H20 (0.1% TFA) from 38% to 68%, v/v). The pure fractions were collected and half of the volatiles were removed in vacuo. The mixture was adjusted to pH=7 with Amberlite IRA-900 (OH) anionic exchange resin and the resin was filtered off. The organic solvent was concentrated in vacuo and the aqueous layer was lyophilized to dryness. The obtained product was further purified by silica gel chromatography (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 70/30) resulting in compound 99 (190 mg). Method A; Rt: 6.09 min. m/z : 369.2 (M+H)+ Exact mass: 368.1, 1H NMR (400 MHz, CHLOROFORM- ) delta ppm 8.35 (1 H, t, J=1.5 Hz), 8.09 – 8.17 (2 H, m), 8.04 (1 H, dt, J=8.0, 1.5 Hz), 7.66 (1 H, t, J=8.0 Hz), 7.54 (1 H, ddd, J=11.5, 6.5, 3.0 Hz), 7.14 – 7.22 (1 H, m), 4.72 (1 H, d, J=8.0 Hz), 3.43-3.60 (1 H, m), 2.32 (3 H, d, J=2.0 Hz), 1.10 (6 H, d, J=6.5 Hz).

According to the analysis of related databases, 875664-41-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; LAST, Stefaan Julien; RABOISSON, Pierre Jean-Marie Bernard; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim Gaston; WO2014/33170; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 69902-83-6, A common heterocyclic compound, 69902-83-6, name is 1-Bromo-2-methyl-3-(trifluoromethyl)benzene, molecular formula is C8H6BrF3, 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[00293] To a solution of l-bromo-2-methyl-3-(trifluoromethyl)benzene (CXXVII) (5.7 g, 23.86 mmol) in CC14 (50 niL) was added NBS (4.24 g, 23.86 mmol) and a catalytic amount of benzoyl peroxide. The reaction mixture was gently refluxed for 1 h. The reaction mixture was cooled to room temperature and the precipitate was removed by filtration. The solution was concentrated under reduced pressure and the crude product was dissolved in hexane and additional precipitate was removed by filtration. The filtrate was concentrated to dryness to give l-bromo-2-(bromomethyl)-3-(trifluoromethyl)benzene (CXXVIII) as an orange oil (7.51 g, 23.62 mmol). 1H NMR (DMSO-d6) delta ppm 4.73 (s, 2H), 7.4 (dd, J=8 Hz, J=8 Hz, 1H), 7.80 (d, J=8 Hz, 1H), 8.02 (d, J=8 Hz, 1H); 19 F NMR (DMSO-d6) delta ppm -57.85 (s, 3F). The crude product was used without further purification for step 2.

The synthetic route of 69902-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; REMPEX PHARMACEUTICALS, INC.; GLINKA, Tomasz; HIGUCHI, Robert; HECKER, Scott; EASTMAN, Brian; RODNY, Olga; WO2012/109164; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 21865-50-9, 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 21865-50-9 as follows.

General procedure: A mixture of starting compound (2.69 mmol), CuCl2.2H2O (10 mol %) in DMSO (5 mL) stirred at 100 C. The reaction progress was monitored by thin layer chromatography (PMA was used for stain solution). The reaction mixture was poured into ice cold water. The crude product was purified by column chromatography using ethyl acetate and petroleum ether as eluent to afford carbazoles.

According to the analysis of related databases, 21865-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dalvi, Bhakti A.; Lokhande, Pradeep D.; Tetrahedron Letters; vol. 59; 22; (2018); p. 2145 – 2149;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 112279-60-4, name is 4-Bromo-2,5-difluoroaniline, 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 112279-60-4, category: bromides-buliding-blocks

A degassed solution of ethyl 3-(trifluoromethanesulfonyloxy)furo [3,2- c]pyridine-2-carboxylate (678 mg, 2.00 mmol), 4-bromo-2,5-difluoroaniline (670 mg, 3.22 mmol), Pd2dba3 (147 mg, 0.160 mmol), Xantphos (97.0 mg, 0.168 mmol) and finely powdered K3PO4 (793 mg, 3.74 mmol) in toluene (7.5 ml) was heated in a sealed tube at 1050C overnight. The reaction mixture was cooled to ambient temperature then diluted with ethyl acetate (15 ml) and filtered through a plug of silica gel (15 ml packed in ethyl ether). After washing the filter cake with more ethyl acetate (20 ml), the filtrate was dried over magnesium sulfate and concentrated in vacuo to give a brown oil. The residue was purified by flash chromatography (silica gel, using using 5:3:2 hexane-methylene chloride-ethyl ether) to afford the title compound as a tan solid (329 mg, 41%).

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

Reference:
Patent; GENENTECH, INC.; WO2008/24725; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 121086-19-9,Some common heterocyclic compound, 121086-19-9, name is 4-Bromo-N-isopropylaniline, molecular formula is C9H12BrN, 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.

N-(4-Bromophenyl)-N-(2-propyl)-3-methyl-2-butenamide Compound 5 A solution of 3,3-dimethylacryloyl chloride (5.56 mL, 50 mmol) in 120 mL of chloroform was added to a solution of 4-bromo-N-(2-propyl)-aniline (Compound 4, 10.4 g, 48.5 mmol) in 400 mL of chloroform over 5 minutes. The reaction mixture was then refluxed overnight. After cooling to room temperature, the reaction mixture was washed with 5% HCl (1*150 mL), saturated, aqueous sodium bicarbonate (1*150 mL) and brine (1*150 mL). The organic phase was dried over anhydrous sodium sulfate and the solvent evaporated in vacuo to afford 13.8 g (96%) of the title compound as a brown solid. 1 H-NMR (300 MHz, CDCl3): d 1.05(d, J=6.8 Hz, 6H), 1.63(s, 3H), 2.08(s, 3H), 4.98(m, 1H), 5.22(br s, 1H), 6.95(d, J=8.5 Hz, 2H), 7.51(d, J=8.6 Hz, 2H).

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

Reference:
Patent; Allergan Sales, Inc.; US6048873; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1159010-96-4, 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. 1159010-96-4 name is 3-Bromo-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, 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 mixture of 4,4,5,5-tetramethyl-2-(2-methylbiphenyl-3-yl)-1,3,2-dioxaborolane (Example 4, Step 1: 20 mg, 0.07 mmol), 3-bromo-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (AstaTech cat SC2711: 17 mg, 0.068 mmol), [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (3 mg, 0.003 mmol) and potassium carbonate (28 mg, 0.20 mmol) in 1,4-dioxane (1 mL) and water (0.5 mL) was degassed and recharged with nitrogen three times. The mixture was then heated and stirred at 110 C. overnight. The crude reaction mixture was purified by prep LCMS (pH 2, acetonitrile/water+TFA) to give the desired product as its TFA salt. LC-MS calculated for C21H21N2(M+H)+: m/z 301.2; found: 301.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 952511-74-9,Some common heterocyclic compound, 952511-74-9, name is 4-Bromo-3-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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-methyl-1,2-benzenediamine (6.89 g, 34.3 mmol), formic acid (60 ml) and 37percent concentrated HCl (150 ml) were heated at 60¡ã C. for 12 h, cooled in an ice-water bath, and slowly adjusted with 28percent concentrated ammonium solution (280 ml) to pH8-9. The solid was collected by filtration, washed with water and dried in air to afford the title compound as a pinkish white solid.1H NMR (400 MHz, DMSO-d6) delta ppm 2.58 (s, 3H) 7.32 (s, 2H) 8.20 (s, 1H) 12.62 (br., 1H); (M+1) 212.94, 1.11 min (LC/MS method A)

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

Reference:
Patent; Diaz, Caroline Jean; Haffner, Curt Dale; Speake, Jason Daniel; Zhang, Cunyu; Mills, Wendy Yoon; Spearing, Paul Kenneth; Cowan, David John; Green, Gary Martin; US2010/222345; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary