Tag: M.W=200-300

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. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H3BrF4

Example 20 Synthesis of TRV 1 166[00146] TRV 1166 (4-(3-(isopropylamino)-4-(trifluoromethyl)phenyl)piperazin-l- yl)(phenyl)methanoneTRV 1166[00147] Scheme for TRV 1 166[00148] 4-bromo-2-fluorobenzotrifluoride (0.5181 g, 2.13 mmol), isopropyl amine (0.22 mL, 2.56 mmol), DIPEA (0.56 mL, 3.2 mmol) and NMP (3 mL) were added to a tube. The tube was sealed and heated overnight at 100 C. After cooling, the reaction mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HCI (2x), saturated NaHC03, H20 and brine before drying with Na2S0 . The material was filtered and concentrated under reduced pressure to give 0.1521 g of crude oil which was a 4:6 mixture of starting material to product, respectively. This material was dissolved in NMP (3 mL), treated with D PEA (0.07 mL, 0.38 mmol) and isopropyl amine (0.2 mL) and heated in a sealed tube at 115 C overnight. After cooling, the reaction mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HC1 (2x), saturated NaHC03, H20 and brine before drying with Na2S04. The material was filtered and concentrated under reduced pressure to give 0.1656 g of crude oil Purification of this material was not required. This aniline (0.1544 g, 0.55 mmol), benzoylpiperazine hydrochloride (0.1496 g, 0.66 mmol) and NaOiBu (0.1586 g, 1.65 mmol) were added to a tube. The tube was evacuated and flushed with argon for three cycles. Toluene (1.7 mL) and NMP (1.0 mL) were then added and the mixture was degassed with argon for 30 minutes. Pd2(dba)3 (0.0101 g, 0.01 1 mmol) and BetaGamma AlphaRho (0.0137 g, 0.022 mmol) were then added, the tube was sealed and heated overnight at 80 C. After cooling, the mixture was diluted with water and EtOAc. The aqueous layer was back-extracted with EtOAc (3x). The combined organic layers were then washed with H20, IN HC1 (2x), saturated NaHC03, H20 and brine before drying with Na2S04. The material was filtered and concentrated under reduced pressure to give a crude oil. Purification of this material via flash chromatography (20 % EtOAc / hexane) gave 0.125 g (58 % yield) of TRV 1166 (4-(3- (isopropylamino)-4-(trifluoromethyl)phenyl)piperazin-l-yl)(phenyl)methanone[00149] NMR (700 MHz, CDC13) delta = 7.46-7.41 (m, 5H), 7.30 (d, J = 8.4 Hz, 1 H), 6.21 (dd, J = 8.4, 2.1 Hz, 1H), 6.16 (s, 1H), 4.12-4.1 1 (m, 1H), 3.93 (br s, 2H), 3.68-3.66 (m, 1H), 3.59 (br s, 2H), 3.33 (br s, 2H), 3.18 (br s, 2H), 1.24 (d, J = 6.2 Hz, 6H).

According to the analysis of related databases, 142808-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TREVENTIS CORPORATION; REED, Mark, A.; YADAV, Arun; BANFIELD, Scott, C.; BARDEN, Christopher, J.; WO2012/119035; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 626-40-4, name is 3,5-Dibromoaniline, 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 626-40-4, category: bromides-buliding-blocks

3,5-Dichlorobenzoyl chloride (90.3 mg, 0.431 mmol) and 3,5-dibromoaniline (91.2 mg, 0.363 mmol) were stirred in THF (2.0 mL) for 1 h.The reaction was then diluted with H2O (~20 mL) and sonicated, and the resulting precipitate was filtered, rinsed with H2O, collected, sonicated with sat. NaHCO3(~10 mL), filtered, rinsed with H2O, and collected.Flash chromatographic purification over silica (4:1 hexanes:EtOAc) afforded 3,5-dichloro-N-(3,5-dibromophenyl)benzamide (217) as an off-white solid (125 mg, 81%).1H-NMR (500 MHz,d6-DMSO)d10.60 (s, 1H), 8.02 (d,J=1.7 Hz, 2H), 7.96 (d,J=1.9 Hz, 2H), 7.90 (t,J=1.9 Hz, 1H), 7.58 (t,J=1.7 Hz, 1H);13C-NMR (125 MHz, CDCl3)d163.02, 139.32, 136.93, 135.94, 132.22, 130.60, 125.69, 123.21, 121.82; ESI-TOF 421.8341m/z[MH]+, C13H8Br2Cl2NO requires 421.8344; RP-HPLC: 97% pure.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Connelly, Stephen; Mortenson, David E.; Choi, Sungwook; Wilson, Ian A.; Powers, Evan T.; Kelly, Jeffery W.; Johnson, Steven M.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3441 – 3449;,
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. 546115-65-5, name is 1-(3-Bromophenyl)cyclopropanamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 546115-65-5

To a solution of l-(4-fluoro-phenyl)-lH-pyrazolo[3,4-c]pyridine-4-carboxylic acid (0.500 g, 1.94 mmol), l-(3-bromophenyl)cyclopropanamine (453 mg, 2.14 mmol) and N,N-diisopropylethylamine (1.73 mL, 9.72 mmol) in DMF (18 mL) is added TBTU (0.780 g, 2.43 mmol). After 2 hours, the mixture is concentrated in vacuo, dissolved in ethyl acetate (200 mL), and washed with 2Nu sodium hydroxide (3 x 100 mL), saturated aqueous ammonium chloride (2 x 100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL). The organic layer is dried over MgS04, filtered through a pad of silica gel eluting with ethyl acetate (3 x 100 mL), and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with a gradient of 50-70% ethyl acetate in heptane to give a solid that is triturated with methylene chloride to afford the title compound as a 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 546115-65-5.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KUZMICH, Daniel; MAO, Can; RAZAVI, Hossein; WO2011/49917; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 393-37-3, name is 5-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Bromo-2-fluorobenzotrifluoride

A mixture of l-bromo-4-fluoro-3-(trifluoromethyl)benzene (5.02 g) and potassiumcyanide (1.38 g) in DMSO (20 ml) was heated at 80 C for 14 h. Water was added and themixture was extracted ether, the organic extracts were dried (MgSO4) and evaporated to givea brown oil. This was dissolved in DMSO (10 ml) and 4 M NaOH (10 ml) and heated at 100C for 16 h. 2 M Hcl (20 ml) was added and the mixture was extracted with DCM (threetimes), the organic extracts were dried (MgSO4), evaporated and purified by chromatography(silica, CH^Ck-MeOH-AcOH as eluent) to give the sub-title compound (1.99 g).MS: ESI (-ve): 268 [M-H]’ 100%.

The synthetic route of 393-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/21759; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 16518-62-0, 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. 16518-62-0 name is 3-Bromo-N,N-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.

EXAMPLE 2 Preparation of 1-(4-chlorobenzyl)-3-dimethyl-amino-6-(3-fluoro-4-isopropoxyphenylamino)benzene (I-123) To a mixture of 3-bromo-1-dimethyl-aminobenzene (0.3 g, 1.5 mmol) and THF (3 mL) were added 4-chlorobenzyl zinc chloride (0.5 M THF solution, 6 mL, 3 mmol), triphenylphosphine (39.3 mg, 0.15 mmol) and palladium acetate (II) (17 mg, 0.08 mmol), and the resulting mixture was heated at reflux for 2 hours. To the reaction mixture was added water (200 mL), and the resulting mixture was extracted with ethyl acetate (200 mL). The extract was washed by brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 1-(4-chlorobenzyl-3-dimethyl-aminobenzene (0.32 g, Yield: 87percent) as colorless oil. 1H-NMR, (delta ppm TMS/CDCl3): 2.89 (6H, s), 3.87 (2H, s), 6.48-6.59 (4H, m), 7.08-7.22 (4H, m).

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

Reference:
Patent; SHIONOGI & CO., LTD.; Kai, Hiroyuki; Endoh, Takeshi; Jikihara, Sae; Horiguchi, Tohru; US9212130; (2015); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 6627-78-7, 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. 6627-78-7 name is 1-Bromo-4-methylnaphthalene, 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 5 L four-necked flask was charged with 461.8 g of 4-bromo-1-methylnaphthalene (I)7.2kg of carbon tetrachloride,375.6 g of N-bromosuccinimide,20.5 g BP0,The temperature was raised to 70 to 78 C (preferably 77 C) and the reaction was refluxed overnight.Point plate,The reaction is complete.Cooled to room temperature,Filter,40 C spin dry solvent.Add 1200 g of ethanol,Heating up to 70 C Paul lh,Cooling to room temperature,Filter,Filter cake washed with ethanol,After draining,Dried at 35 C to give 500 g of 4-bromo-1-bromomethylnaphthalene (II)The two-step yield was 79% (based on 1-methylnaphthalene).

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

Reference:
Patent; Shanghai Ya Ben Chemical Co., Ltd.; Zhou, Yu; Xiao, Fangliang; Shi, Wei; Xu, Meng; (7 pag.)CN106366018; (2017); A;,
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. 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-1,3-diethyl-5-methylbenzene

Into an oven-dried 35 ml_ carousel reaction tube fitted with a magnetic stirrer bar was added the palladium source, APhos (4-di-ferf-butylphoshanyl-N,N-dimethyl-aniline, 0 – 20 mol%), 1 ,2,4,5- tetrahydropyrazolo[1 ,2-d][1 ,4,5]oxadiazepine-7,9-dione (1.2 equiv.) and K3PO4 (2.1 equiv.) under an atmosphere of N2 gas. A solution of 2-bromo-1 ,3-diethyl-5-methyl-benzene (DEMBB, 1 equiv.) and mesitylene (0.25 equiv. as an internal standard) in 1 ,4-dioxane (1 – 3 ml) was purged of oxygen by bubbling with N2 gas for 20 mins and then transferred to the reaction tube which was then placed immediately into the pre-heated carousel at 1 10 C and stirred for 6 h. Sampling procedure: A small aliquot of the reaction mixture was quenched with HCI (aq, 1 M) and extracted into EtOAc. The conversion was determined by NMR spectroscopy and/or GC analysis against mesitylene as an internal standard, or 1 , 3, 5-trimethoxybenzene as an external standard. The above general procedure (example 3) was used to obtain the results referred to in Table 2 below. (0136) Table 2 – Summary of results comparing differing palladium catalysts with the APhos ligand

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; SYNGENTA PARTICIPATIONS AG; MORRIS, James, Alan; SALE, David, Alexander; SHAFIR, Alexandr; GONU, Mallikharjuna; BILAL, Iffat; (27 pag.)WO2019/110613; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2255-80-3,Some common heterocyclic compound, 2255-80-3, name is 4-Bromo-7-methylbenzo[c][1,2,5]thiadiazole, molecular formula is C7H5BrN2S, 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-7-methylbenzo[c][l,2,5]thiadiazole (0.25 g, 1.1 mmol) was dissolved in AcOH (12 ml) and H2SO4 (1.7 ml). [CAUTION: Exothermic]. The solution was then treated with chromium (VI) oxide (1.5 g) portionwise and stirred for 30 mins. The reaction was then poured onto ice and allowed to warm to room temperature. The aqueous layer was then extracted with DCM (3 x 30 ml). The aqueous layer was left overnight and the precipitate filtered and washed with water (3 x 2 ml) to afford the title compound as a white solid (0.085 g, 30 %); vmax(thin film) 3100 – 3300 (broad – OH), 1682 (C=O), 1680, 1525, 1312, 1289, 1193 cm-1; deltaH(500 MHz, (CD3)2CO) 8.31 (IH, d, / 8, Ar-H), 8.15 (1eta, d, / 8, Ar-H), 2.09 (1eta, s, CO2H); deltaC (126 MHz, (CDs)2CO) 165.1 (C=O), 154.8 (C=N), 152.6 (C=N), 134.7 (Ar-C), 132.6 (Ar-Q, 124.2 (ipso-Ar-Q, 120.1 (ipso-Ai-Q; m/z (ES”) 259 ([81Br]M”), 257 ([79Br]M”); HRMS (ES”) Found M”, 256.90248 (C7H279BrN2O2S requires 256.90258).

The synthetic route of 2255-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF DURHAM; WO2009/34396; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 22385-77-9, The chemical industry reduces the impact on the environment during synthesis 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, I believe this compound will play a more active role in future production and life.

1-Bromo-3,5-tert-butylbenzene (2.50 equivalents, CAS: 22385-77-9) in dry THF is added dropwise to activated magnesium turnings suspended in dry THF under N2 atmosphere. After addition, the mixture is refluxed for a few hours until 1-bromo-3,5-tert-butylbenzene (CAS: 22385-77-9) is consumed completely and the mixture becomes dark brown. The resulting Grignard reagent is slowly added to cyanuric chloride (1.00 equivalent in dry toluene, CAS: 108-77-0) at room temperature (RT) (the cyanuric chloride was previously prepared in another flask). After addition, the mixture is refluxed overnight and cooled to RT. The crude product 2- chloro-4,6-bis(3,5-di-tert-butylphenyl)-1 ,3,5-triazine is extracted with DCM/brine and recrystallized from EtOH/DCM (20:1 ) to yield a white solid.

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-3,5-di-tert-butylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CYNORA GMBH; SZAFRANOWSKA, Barbara; PINGEL, Patrick; BERGMANN, Larissa; AMBROSEK, David; KASPAREK, Christian; (0 pag.)WO2019/162332; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 444-14-4, name is 2-Bromo-4,6-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 444-14-4, HPLC of Formula: C6H4BrF2N

Commercially available bromodifluoroaniline (11) is treated with di-tert-butyldicarbonate to give protected aniline 12. Alkylation of aniline 12 gives the N-ethyl derivative 13, which is converted to the lithium derivative by metal halogen exchange, and added to the Boc-protected aziridine 3a under copper catalysis, yielding intermediate 14. The acetal protecting group is removed and the resulting diol 15 is converted to epoxide 16 using well-known procedures.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87752; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary