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. 875664-41-8, name is 3-Bromo-4,5-difluoroaniline, A new synthetic method of this compound is introduced below., name: 3-Bromo-4,5-difluoroaniline

This acid (700 mg,2.33mmol), 3-aminobenzonitrile (347.8mg, 2.91 mmol), HATU (1108mg, 2.9l4mmol) andDIPEA (1 .2mL, 6.99 mmol) was dissolved in DMF (7 mL) and the mixture was stirred at roomtemperature for 16 h. The mixture was poured in 100 mL ice water and was extracted withEtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered andconcentrated in vacuo. The residue was purified on a silica using a gradient eluent HeptaneEtOAc 100-0 -> 50-50. The product fractions were collected and concentrated in vacuo. The product was crystallized from 2-propanol, filtered off and dried in vacuo, yielding compound 158 (518 mg) as a white solid.Compound 205 (893 mg) was prepared similarly as described for compound 158 using 3-bromo-4,5-difluoroaniline (970 mg, 4.663 mmol) instead of 3-aminobenzonitrile and stirring at 60C during 18 h. The obtained residue was warmed with CH2C12/heptanes and the white solid collected by filtration. Method A: Rt: 1.79 mm mlz: 489.9 (M-H)- Exact mass: 488.98. ?H NMR (400 MHz, DMSO-d6) oe ppm 1.08 (d, J=7.0 Hz, 3 H), 3.84 – 3.99 (m, 1 H), 3.92 (s, 3 H), 7.36 (d,J=1.8 Hz, 1 H), 7.67 (d, J=1.5 Hz, 1 H), 7.80 – 7.93 (m, 2 H), 8.19 (br. s., 1 H), 10.30 (s, 1 H). Differential scanning calorimetry: From 30 to 300 C at 10C/mm: peak at 196.72 C.

The synthetic route of 875664-41-8 has been constantly updated, and we look forward to future research findings.

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;,
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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. 40422-70-6, name is 1-Bromo-3-(2-bromoethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-3-(2-bromoethyl)benzene

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 (16.3 ml, 26 mmol) was added dropwise at -78 C and stirred for 15 minutes. A solution of 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 for 1 h followed by stirring at rt for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted using ethyl acetate. The combined organic layer was dried over sodium sulfate and concentrated and 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.

According to the analysis of related databases, 40422-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRAMELD Kenneth; OWENS Timothy; WO2015/195950; A1; (2015);,
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Electric Literature of 1177559-63-5, 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 1177559-63-5 as follows.

To a stirred solution of (3-bromo-2-fluorophenyl)methanamine hydrochloride (15.0 g, 62.5 mmol, 1 equiv) and 1 ,1 -dimethoxypropan-2-one (9.58 g, 81 .25 mmol, 1 .3 equiv) in DCE (150 mL) was added sodium triacetoxyborohydride (17.22 g, 81 .25 mmol, 1 .3 equiv) at room temperature and the mixture was stirred overnight. 30% aqueous K3P04 (pH=14) was added to the reaction mixture, the layers were partitioned and the aqueous layer was extracted with EtOAc (2 x 200 mL), and the organics were combined and washed with brine ( 100 mL), and dried over Na2S04. The organic solvent was concentrated to give the N-(3- bromo-2-fluorobenzyl)-1 ,1 -dimethoxypropan-2-amine as a colorless liquid (19 g, crude). LC-MS (ES) m/z = 306.2, 308.0 [M+H]+. NMR (400 MHz, DMSO-d6) delta ppm 0.94 (d, J = 6.4 Hz, 3 H), 1 .89 (br.s, 1 H), 2.62 (t, J = 6 Hz, 1 H), 3.22 (s, 3 H), 3.25 (s, 3 H), 3.73 – 3.76 (m, 1 H), 3.80 – 3.84 (m, 1 H), 4.06 (d, J = 5.6 Hz, 1 H), 7.09 (t, J = 8 Hz, 1 H), 7.44 (t, J = 6.8 Hz, 1 H), 7.53(t, J = 7.2 Hz, 1 H).

According to the analysis of related databases, 1177559-63-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; KETHIRI, Raghava Reddy; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (162 pag.)WO2018/15879; (2018); A1;,
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41825-73-4, name is 2-Bromo-4,6-dimethylaniline, 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. Formula: C8H10BrN

In 100mL Schlenk flask 2-bromo-4,6-dimethyl aniline (manufactured by Kanto Chemical Co., Inc.) (4.97g, 24.9mmol) and di-tert-butyl dicarbonate (manufactured by Kanto Chemical Co., Inc.) (13.6g, 62.1mmol) They were weighed, and dissolved by adding dehydrated toluene (manufactured by Kanto Chemical Co., Inc.) (35 mL). Introducing a reaction vessel in an oil bath preset at 90 C., and reacted for 33 hours. After completion of the reaction, the solvent was removed by silica column chromatography (hexane: ethyl acetate = 20: 1) as a white solid (2-bromo-4,6-dimethylphenyl) – carbamic acid tert-butyl ester was isolated ( 5.10g, 17.0mmol, 68%).

The synthetic route of 41825-73-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokyo Institute of Technology; JapanPolychemCo., Ltd.; Osakada, Kotaro; Takeuchi, Daisuke; Takano, Shigenaga; Uchino, Hideshi; Kobayashi, Minoru; (93 pag.)JP2015/117237; (2015); A;,
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These common heterocyclic compound, 60956-23-2, name is 1,2-Dibromo-4-methylbenzene, 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. Safety of 1,2-Dibromo-4-methylbenzene

General procedure: A 12 mL vial was charged with [Pd(cinnamyl)Cl]2(1,5 mol%), dppp (3 mol%). and a stirring bar. Then, 1,2-dibromo-benzene(0.5 mmol), DBU (4.0 eq) and toluene (3 mL) were injected by syringe underargon. The vial (or several vials) was placed in an alloy plate, which wastransferred into a 300 mL autoclave of the 4560 series from Parr Instrumentsunder argon atmosphere. After flushing the autoclave three times with CO, apressure of 10 bar of CO was adjusted at ambient temperature. Then, thereaction was performed for 16-24 h at 140 oC. After the reactioncompleted, the autoclave was cooled down with ice water to room temperature andthe pressure was released carefully. After evaporation of the organic solventthe residue was adsorbed on silica gel and the crude product was purified bycolumn chromatography using EA/pentane(1:1) for phthalimides and MeOH/EA (1:40) for the amides as eluent.

The synthetic route of 1,2-Dibromo-4-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Jianbin; Natte, Kishore; Wu, Xiao-Feng; Tetrahedron Letters; vol. 56; 2; (2015); p. 342 – 345;,
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Reference of 90562-10-0, 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. 90562-10-0 name is 1-Bromo-4-(3-bromopropyl)benzene, 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.

Compounds 2 (40 mg, 0.14 mmol) and 7 (27.6 mg, 0.15 mmol) were dissolved in 1.5 mL of acetonitrile and then potassium carbonate (20.7 mg, 0.15 mmol) was added to the solution. After reflux for 1 h, potassium carbonate was removed by filtration. The solvent was removed in vacuo. The residue was purified by chromatography on silica gel using chloroform-methanol (40:1) as the eluent to obtain compound 9 (52 mg, 94%) as a colorless powder. 1H NMR (400 MHz, CDCl3): delta 1.10-1.32 (m, 4H), 1.65-1.85 (m, 5H), 2.07-2.25 (m, 2H), 2.35-2.55 (m, 6H), 2.34 (t, J=7.6 Hz, 2H),2.58 (t, J=7.6 Hz, 2H), 2.70-2.80 (m, 2H), 3.30-3.40 (m, 1H), 3.90-4.05 (m, 1H), 7.05 (d, J=7.8 Hz, 2H), 7.39 (d, J=7.8 Hz, 2H). HRMS (DART) m/z calcd for C19H30BrN2O (M+H)+, 381.1542; found 381.1548.

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

Reference:
Article; Ogawa, Kazuma; Masuda, Ryohei; Mishiro, Kenji; Wang, Mengfei; Kozaka, Takashi; Shiba, Kazuhiro; Kinuya, Seigo; Odani, Akira; Bioorganic and Medicinal Chemistry; vol. 27; 10; (2019); p. 1990 – 1996;,
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Electric Literature of 90562-10-0, A common heterocyclic compound, 90562-10-0, name is 1-Bromo-4-(3-bromopropyl)benzene, molecular formula is C9H10Br2, 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.

EXAMPLE 101. Synthesis of l-[3-(4-Bromo-Phenyr)-Propyll-Pyrrolidine(Intermediate 51)51[0300] To a solution of intermediate 50 (Example 100) (3.5 g, 13 mmol) in dioxane (40 mL) was added pyrrolidine (2.1 mL, 25 mmol), followed by cesium carbonate (8.2 g, 25 mmol). The mixture was stirred at room temperature for 15 h and poured into water. The mixture was extracted with ethyl acetate and the organic layer separated, washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (10% MeOH/DCM to 25% MeOH and 2% TEA/DCM) to afford the title compound (1.8 g, 53%) as a pale orange oil. [0301] 1H NMR (500 MHz, DMSOd6): delta 1.60-1.65 (m, 6H), 2.35 (t, J= 13 Hz, 2H), 2.35-2.43 (m, 4H), 2.57 (t, J= 7.7 Hz, 2H), 7.16 (d, J= 8.3 Hz, 2H)3 7.44 (d, J= 8.4 Hz, 2H)

The synthetic route of 90562-10-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); A1;,
Bromide – Wikipedia,
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Reference of 28148-04-1, 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. 28148-04-1, name is 1,3-Dibromo-2-methylpropane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The beta- lactam carbonyl compound of the formula shown in C6H5-COCH2CONH-CH31.0mmol added 50 ml round bottomFlask, and then followed by adding K2CO32.4mmol, tetrabutylammonium bromide 0.07mmol, ammonium acetate 1.2mmol, 1,3- dibromo-2-Methyl propane 1.2mmol and 30mL of deionized water and mix well. The reaction was continued stirring at 30 deg C 8.0 hours, stoppedThe reaction, was filtered, dried, purified by recrystallization methanamine obtained after 5-benzoyl-6- methyl-3,4-dihydro-pyran-3, 87% yield of product.

The synthetic route of 1,3-Dibromo-2-methylpropane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huaihua University; Xiang, Dexuan; Liang, Chunhua; Liu, Yilin; Xiang, Bailin; Zhang, Li; (9 pag.)CN105541770; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

90562-10-0, name is 1-Bromo-4-(3-bromopropyl)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. Quality Control of 1-Bromo-4-(3-bromopropyl)benzene

EXAMPLE 23 3-[(N-(3-(4-Bromo-phenyl)-propyl)-piperidin-3-yl)-methyl]7,8dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-hydrochloride Prepared from 3-[(piperidin-3-yl)-methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one and 3-(4-bromophenyl)propyl bromide analogously to Example 1. Yield: 34.8% of theory, Melting point: 100-104 C.

The synthetic route of 90562-10-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim GmbH; US5175157; (1992); A;,
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Related Products of 112279-60-4,Some common heterocyclic compound, 112279-60-4, name is 4-Bromo-2,5-difluoroaniline, molecular formula is C6H4BrF2N, 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 197 5,8-Difluoro-1,2-dihydro-6-(3-nitrophenyl)-2,2,4-trimethylquinoline (Compound 297, structure 83 of Scheme XXI, where R1 =R3-5 =R7 =R9 =H, R2 =nitro, R6 =R8 =fluoro) This compound was prepared by the same procedure as described in the synthesis of Compound 291 (EXAMPLE 191) from 4-bromo-2,5-difluoroaniline (32 mg, 0.13 mmol) and 3-nitrobenzeneboronic acid (167 mg, 1.0 mmol) to afford 3 mg (10%) of Compound 297 as a colorless oil. Data for Compound 297: 1 H-NMR(400 MHz, CDCl3) 8.33 (t, J=1.6, 1H), 8.14 (dd, J=8.0, 1.6, 1H), 7.78 (d, J=8.0, 1H), 7.57 (t, J=8.0, 1H), 6.94 (dd, J=10.8, 6.3, 1H), 5.37 (s, 1H), 4.16 (bs, 1H), 2.17 (dd, J=7.0, 1.3, 3H), 1.34 (s, 6H).

The synthetic route of 112279-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;,
Bromide – Wikipedia,
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