Tag: M.W=100-200

5433-01-2, 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. 5433-01-2, name is 1-Bromo-3-isopropylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 1 (15mg, 0.079mmol), 2 (30mg, 0.158mmol) and Cs2CO3 (128mg, 0.395mmol) in DMF (lmL) were added 2 mg of Pd(dba)2 and 2 mg of Xantphos. The suspension was degassed under vacuum and purged with N2 several times. The mixture was stirred at 120 C for 6h. LCMS showed the SM was consumed completely. Then the reaction mixture was diluted with EA (10mL) and washed with brine (2mL) twice. The organic solution was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified by p-TLC to give the desired compound Compound 220 (5mg, yield: 20.8%). LCMS: m/z, 309.1 (M+H)+; 1HNMR:(d-CDCl3 (400MHz): delta 8.54~8.55(m, 1H), 7.61~7.65(m, 1H), 7.44(d, J=7.6, 1H), 7.21~7.24(m, 1H), 7.12(t, J=5.8, 1H), 6.56(d, J=7.6, 1H), 6.32~6.36(m, 2H), 3.84(s, 1H), 3.77(s, 1H), 3.45~3.53(m, 2H), 2.75~2.82(m, 1H), 2.56~2.66(m, 1H), 2.37~2.53(m, 1H), 1.19(d, J=4.8,6H).

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; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; BALDWIN, John J.; WU, Chengde; SHEN, Chunli; WO2014/124560; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

556-96-7, 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. 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

N-Hexyl-3,5-dimethylaniline (, entry 1) Using the general procedure, 5-bromo-m-xylene (136 muL, 1.0 mmol) was coupled with n-hexylamine (198 muL, 1.5 mmol). Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (20:1) as eluent afforded the desired product as a colorless oil (185 mg, 90% yield).

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; Buchwald, Stephen L.; Klapars, Artis; Antilla, Jon C.; Job, Gabriel E.; Wolter, Martina; Kwong, Fuk Y.; Nordmann, Gero; Hennessy, Edward J.; US2003/65187; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

38573-88-5, 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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 2Preparation of (4-bromo-2,3-difluorophenyl)trimethylsilaneDiisopropylamine (7.86 grams (g), 78 mmol) was dissolved in tetrahydrofuran (THF; 104 mL) and cooled to -75¡ã C. utilizing a dry ice/acetone bath.A solution of n-BuLi (2.5 M in hexanes; 22.80 mL, 57.0 mmol) was added dropwise, and the solution was again cooled to -75¡ã C. 1-Bromo-2,3-difluorobenzene (10 g, 51.8 mmol) was dissolved in THF (25.9 mL), and the solution was added dropwise keeping the temperature below -60¡ã C.The reaction mixture was then allowed to warm to -15¡ã C. before cooling again to -75¡ã C. TMSCl (7.29 mL, 57.0 mmol) was then added dropwise, and the reaction mixture was allowed to warm to 25¡ã C. and then concentrated under vacuum.The residue was partitioned between ethyl acetate (EtOAc) and H2O.The organic phase was washed twice more with H2O and concentrated.Kugelrohr distillation at 88¡ã C. provided the product in greater purity but an impurity was distilling at that temperature.Kugelrohr distillation of that purified distillate at 75¡ã C. led to purer product but some product was left in the pot.This process yielded the title compound as a clear oil (3.0 g, 21.83percent, 90percent purity): 1H NMR (300 MHz, CDCl3) delta 7.28 (ddd, J=7.8, 5.2, 1.3 Hz, 1H), 6.98 (ddd, J=8.0, 4.8, 1.9 Hz, 1H), 0.32 (s, 9H); EIMS m/z 264, 266.

The synthetic route of 38573-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epp, Jeffrey B.; Lowe, Christian T.; Renga, James M.; Schmitzer, Paul R.; Eckelbarger, Joseph D.; Guenthenspberger, Katherine A.; Siddall, Thomas L.; Yerkes, Carla N.; Fischer, Lindsey G.; Giampietro, Natalie C.; Kister, Jeremy; Roth, Joshua; US2013/5574; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

51437-00-4, Adding some certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4.

Example 10A Methyl N-(4-fluoro-3-methylphenyl)piperidine-4-carboxylate starting with 10.6 g (74.0 mmol) of methyl piperidine-4-carboxylate and 4.67 g (24.7 mmol) of 5-bromo-2-fluorotoluene, the general procedure [E] gives 2.74 g (40% of theory) of product. HPLC (method 1): Rt=3.48 min Examples 11A to 17A from the table below can be prepared in accordance with the general procedure [E]. General Procedure [F]: Hydrolysis of the N-arylpiperidine-4-carboxylic Esters 1.0 equivalent of the N-arylpiperidine-4-carboxylic ester is dissolved in dioxane, and 2.0 equivalents of 1N aqueous sodium hydroxide solution are added. The mixture is stirred at 80 C. for 16 hours, and after the reaction has ended (the reaction is monitored by analytical HPLC) the mixture is concentrated. The residue is then taken up in water and adjusted to pH=5 using 1N hydrochloric acid. The resulting precipitate is filtered off, washed with a little water and cyclohexane and dried at room temperature under high vacuum. If the purity of the product is not high enough, the product is purified by preparative HPLC on an RP phase.

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 51437-00-4.

Reference:
Patent; Bayer HealthCare AG; US2007/281953; (2007); A1;,
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 38573-88-5 as follows. 38573-88-5

Intermediate 25; 4-(2,3-Difluorophenyl)-3-butyn-1-ol; To a solution of 1-bromo-2,3-difluorobenzene (10.0 g, 51.82 mmol, Aldrich) in dimethylamine (200 ml) under nitrogen were added Bis(tripheylphenylphosphine)palladium(II) dichloride (0.73 g, 1.037 mmol), copper(I) iodide (0.1 g, 0.525 mmol) and 3-butyn-1-ol (11.76 ml). The temperature was raised from ambient to 65¡ã C. and held there with stirring for 20 h, after which the mixture was cooled and all volatiles removed by rotary evaporation. The residue was partitioned between a mixture of 2N HCl (400 ml), brine (100 ml) and dichloromethane (400 ml). A second 100 ml dichloromethane extract and the layers were separated and aqueous was washed with DCM (100 ml). Extracts were combined and the mixture passed through a hydrophobic frit and evaporated under reduced pressure to give a dark brown oil. This oil was purified using a CombiFlash.(R). Companion.(R). 330 g Redisep.(R). silica column eluting with a gradient of cyclohexane:ether (0 to 100percent) affording the title compound as a light orange oil (9.149).H.p.l.c. Rt=2.76 min.1H nmr (CDCl3) delta: 1.88 (1H, t), 2.75 (2H, t), 3.86 (2H, q), 7.01 (1H, m), 7.10 (1H, m), 7.17 (1H, m).

According to the analysis of related databases, 38573-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Camus, Laure; Chudasama, Reshma; Day, Caroline Jane; Deshmukh, Deepali; Gleason, John Gerald; Harling, John David; Lee, Chao-Pin; Saklatvala, Paula; Senger, Stefan; Vallance, Sarah; Watson, John; Watson, Nigel Stephen; Young, Robert John; Yuan, Barbara; US2008/306045; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

3814-30-0, 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. 3814-30-0, name is (Bromomethyl)cyclopentane, A new synthetic method of this compound is introduced below.

Preparation 78: 6-Bromo-1 -(cyclopentylmethyl)-2-(1 -methyl-1 H-pyrazol-4-yl)-1 H- pyrrolo[3,2-c]pyridine; [00248] Sodium hydride (60% in mineral oil, 10.8mg, 0.271 mmol) was added to a solution of 6-bromo-2-(1 -methyl-1 H-pyrazol-4-yl)-1 H-pyrrolo[3,2-c]pyridine (Preparation 22, 50mg, 0.180mmol) in DMF (780ml_). The reaction mixture was then stirred for 15 minutes at room temperature before the addition of (bromomethyl)cyclopentane (44mg, 0.271 mmol). The reaction mixture was then stirred overnight at room temperature and for 24 hours at 60C. Sodium hydride (60% in mineral oil, 5mg, 0.125mmol) was added and the reaction was stirred for another 7 hours at 60C. The reaction mixture was then diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure. The crude was purified via Biotage silica gel column chromatography eluting with (DCM/EtOAc 99/1 to 80/20) to afford the title product as a colourless oil (45mg, 69%). 1 H NMR (500 MHz, CDCI3) d 1 .10-1 .19 (m, 2H), 1 .46-1 .64 (m, 6H), 2.24-2.33 (m, 1 H), 4.03 (s, 3H), 4.09 (d, J = 7.6Hz, 2H), 6.53 (d, J = 0.9Hz, 1 H), 7.45 (t, J = 0.9Hz, 1 H), 7.59 (s, 1 H), 7.68 (s, 1 H), 8.60 (d, J = 0.9Hz, 1 H). LC (Method B)-MS (ESI, m/z) fR 3.03 min, 359 [(M+H+), 100%].

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; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1647-26-3 name is 1-Bromo-2-cyclohexylethane, 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. 1647-26-3

Combine 6- (4-Piperidin-3-yl-phenoxy)-nicotinamide (free base compound of example 322) (0.0255g, 0.0858 MMOL), 1-BROMO-2-CYCLOHEXYLETHANE (0.0150 mL, 0.0958 mmol), and potassium carbonate (0.0245 g, 0.177 mmol) in dimethylformamide (1.0 mL) and stir for 10 min. Purify the reaction mixture by ion exchange chromatography (SCX resin, METHANOL- 2 M AMMONIA/METHANOL) and silica gel chromatography (15: 1 No. 10: 1 ethyl acetate: methanol) to provide 0.0146 g (42%) of the title compound as an off-white foam: high resolution mass spectrum (electrospray): m/z calc for C25H34N302 408. 2651, found 408.2661 ; H NMR (methanol-d4): 8.61 (s br, 1H), 8. 28 (d, 1H, J= 7.8 Hz), 7.36 (d, 2H, J= 7.8 Hz), 7.12 (d, 2H, J= 7.8 Hz), 7.01 (d, 1H, J = 8.3 Hz), 3.07 (d, 2H, J = 10.2 Hz), 2.89 (t, 1H, J= 11.2 Hz), 2.55-2. 42 (M, 2H), 2.15-1. 93 (m, 4H), 1.93-1. 64 (m, 8H), 1.63-1. 43 (m, 4H), 1.40-1. 15 (m, 8H), 1.07-0. 86 (m, 3H).

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

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/26305; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

202865-83-6,Some common heterocyclic compound, 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, molecular formula is C7H6BrF, 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 solution of 1 -(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1H-pyrazol-4-ylboronic acid (50 mg, 0.10 mmol), 1-bromo-3- fluoro-5-methylbenzene (23 mg, 0.12 mmol), Pd(PPh3)4 (12 mg, 0.10 mmol), Na2003 (54 mg, 0.51 mmol) in degassed 1,4-dioxane and H20 (4:1, 2.1 mL) was heated at 85 C for 18 hours. LiOH (12.4 mg, 0.52 mmol) was added and the reaction was heated at 90 O under microwave radiation for 45 minutes. 1 N HCI (1 mL) was added, followed by water (5 mL) and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by semi-prep H PLC-MS (column X-Bridge 30×50) using a solution of MeCN in water (containing 10 mM of NH4CO2H) (60 to 80%). The product was lyophylised and afforded the title compound (13 mg, 0.024 mmol, 24%) as a pale yellow solid. 1H NMR (500 MHz, DMSO) O 8.21 (d, J= 2.0 Hz, 1H), 8.02 (dd, J= 8.5, 2.0 Hz, 1H), 7.75 (d, J= 8.5 Hz, 1H), 7.13 (5, 1H), 7.11 (d, J= 9.9 Hz, 1H), 7.07 (d, J= 9.7 Hz, 1H),3.35 (hept, J= 6.7 Hz, 1H), 2.36 (5, 3H), 2.31 (5, 3H), 1.24 (d, J= 6.7 Hz, 6H); MS (mlz):536.0 [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 1-Bromo-3-fluoro-5-methylbenzene, its application will become more common.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M. Arshad; CIBLAT, Stephane; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu, Jr.; SRIVASTAVA, Sanjay; SHIPPS, Gerald W.; COOPER, Alan B.; OZA, Vibha; KOSTURA, Matthew; LUTHER, Michael; LEVINE, Jedd; (253 pag.)WO2018/102452; (2018); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4. 51437-00-4

In the case of Q10-Br, the desired 2-fluoro-5-phenyl-toluene (S1=F) was prepared from phenylboronic acid and 2-fluoro-5-bromo-toluene via a Suzuki reaction, analogously to procedure A2. See scheme A3.

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 4-Bromo-1-fluoro-2-methylbenzene.

Reference:
Patent; Duphar International Research B.V.; US6225312; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 54879-20-8, name is 2-Bromo-3-methylaniline, molecular formula is C7H8BrN, 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. 54879-20-8

EXAMPLE 7 Preparation of 7-methyl-8-bromo-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride STR33 2-Bromo-3-methylphenylhydrazine hydrochloride (23 g) was prepared as described for 2-bromo-4-methylphenylhydrazine hydrochloride in Example 4, except using 2-bromo-3-methylaniline as starting material. STR34 6-Methyl-7-bromotryptamine hydrochloride was prepared (2.42 g) as described for 5-methyl-7-bromotryptamine hydrochloride in Example 4, except using 2-bromo-3-methylphenylhydrazine hydrochloride as starting material. STR35 A suspension of azalactone (prepared as described in Example 1) (3.63 g, 14.7 mmol.) and 6-methyl-7-bromotryptamine hydrochloride (4.25 g, 4.21 mmol.) in 1N HCl (150 mL) was heated to reflux for 18 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, neutralized with saturated aqueous potassium carbonate solution and extracted with chloroform. The combined organic layers were concentrated under reduced pressure and the residue chromatographed on silica gel (ethyl acetate/0.2percent NH4 OH as eluent). The fractions containing product were pooled and concentrated under reduced pressure. The residue was dissolved in ethyl acetate containing 1percent methanol and treated with dry HCl.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54879-20-8, its application will become more common.

Reference:
Patent; Eli Lilly and Company; US5635528; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary