Tag: M.W=200-300

Application of 45762-41-2,Some common heterocyclic compound, 45762-41-2, name is 4-Bromo-2-ethylaniline, 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.

EXAMPLE 1: SYNTHESIS OF COMPOUNDS COMPOUND 1 : 2-(1,8-DIETHYL-6-PHENYL-1,3,4,9-TETRAHYDRO-PYRANO[3,4-B]INDOL-1- YL)-ETHANOL I. A. SYNTHESIS OF N-(4-BROMO-2-ETHYL-PHEHYL)-2-HYDROXIMINO-ACETOAMIDE To a suspension of 4-bromo-2-ethylaniline (50.0 g, 250 mmol) in water (1000 mL) was added concentrated hydrochloric acid (25 mL), sodium sulfate (220 g), and hydroxylamine hydrochloride (56.25 g), followed by addition of chloral hydrate (44.0 g). The reaction mixture was heated to 90C using an oil bath for 1 hour. After cooling down to room temperature, it was extracted with ethyl acetate. Extract was dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (31.1 g, 46% YIELD). 1H NMR (DMSO-d6) 5 12.24 (s, 1H), 9.56 (s, 1H), 7. 68 (s, 1H), 7.41 (m, 3H), 2. 58 (q, 2H), 1.11 (t, 3H). 47. A. Synthesis of N-(4-Bromo-2-ethyl-phenyl)-2-hydroxyimino-acetamide Following the procedure of example 36. A. except using 4-bromo-2-ethylaniline as the aniline component afforded the title compound as a solid. ESI (-) MS m/e=269 (MH-).

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-2-ethylaniline, its application will become more common.

Reference:
Patent; SALMEDIX, INC.; WO2005/33112; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1137142-58-5,Some common heterocyclic compound, 1137142-58-5, name is 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, molecular formula is C4H2BrN3S, 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.

Intermediate 19; 2-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole; A mixture of 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (1.0 g, 4.90 mmol) and 4- fluorophenol (2.2 g, 19.60 mmol) was heated under microwave irradiation at 135C for 3.5 hours. On cooling, the mixture was diluted with dichloromethane (7 mL), adsorbed in silica and purified by column chromatography (Biotage/Flash, silica, methanol:dichloromethane 0.2:9.8 to 2:8) to give 2-(4-fluoro-phenoxy)- imidazo[2,1-b][1 ,3,4]thiadiazole as a white solid (610 mg, 53% yield).1H-NMR (300 MHz, CDCI3): delta 7.54 (d, J = 1.3 Hz, 1 H), 7.29 (m, 2H), 7.21 (d, J =1.2 Hz, 1 H), 7.14 (m, 2H).MS (ES+) m/z 236 (M+H)+ (MW: 235.24).

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

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); WO2009/40552; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 937046-98-5, A common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, molecular formula is C6H5BrN4, 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.

Intermediate B (230 mg, 1.08 mmol) and the product from step 2 (396 mg, 1.30 mmol) were dissolved in 5 mL of 3:2 dioxane:toluene and degassed via a vacuum/N2 purge (3 cycles). 1 ,1′-Bis(diphenylphosphino)ferrocenepalladium(ll) chloride-dichloromethnane complex (39 mg, 0.05 mmol) was added followed by 2.2 mL of 2M aqueous Na2CO3 and the mixture was heated with stirring to 85 0C overnight. The dark green reaction mixture was cooled to room temp, filtered through a Celite pad and the pad washed well with EtOAc. The organic phase was washed with water, 2M aqueous Na2CO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by lsoc Red-Sep 40, 80% – 100% EtOAc/hexanes to give 173 mg (41%) of the title compound. 1H-NMR (DMSO-cfe) .8 7.90 (s, 1 H), 7.75 (bs, 2H), 7.61, (S, 1H), 7.53 (d, 1 H), 7.28 (t, 1 H), 7.02 (d, 1 H), 6.97 (d, 1 H), 6.83 (dd, 1H) 3.45 (m, 4H), 3.16 (m, 4H), 1.43 (s, 9H); LC-MS [M+H]+ = 395.10, RT = 2.71 min.

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; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 33070-32-5, 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. 33070-32-5 name is 5-Bromo-2,2-difluorobenzodioxole, 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 250 mL round bottom flask with stir bar was charged with toluene (100 mL), and the solvent was sparged with N2 for one hour. Trisodium phosphate (20.75 g, 127 mmol) was added, followed by bis(dibenzylideneacetone)palladium (0.970 g, 1.68 8 mmol). A solution of tri-tert-butylphosphine (0.683 g, 3.38 mmol) was added over 10 minutes via syringe, and the suspension was stirred for 50 minutes at 25C. 5-Bromo-2,2-difluorobenzo[dj[1,3jdioxole (10 g, 42.2 mmol) was added, and after stirring for 50 minutes at 25 C, ethyl 2-cyanoacetate (9.55 g, 84 mmol) was added over 5 minutes, followed by the addition of 1.5 mL of water. The reaction was heated at 75 C for 12 hours. Three additional vials were set up as described above. After completion of the reaction, all four reaction mixtures were combined. The reaction was cooled to 25 C and filtered over diatomaceous earth. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 5/1) to provide the title compound (24.5 g, 48.5 % yield). ?H NMR (400 MHz, DMSO-d6) 6 ppm 1.15 – 1.23 (m, 3 H) 4.13 – 4.29 (m, 2 H) 7.30 (dd, J=8.38, 1.76 Hz, 1 H) 7.46 – 7.55 (m, 2 H).

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

Reference:
Patent; ABBVIE S.A.R.L.; GALAPAGOS NV; CHAN, Vincent S.; KYM, Philip R.; SHEKHAR, Shashank; WANG, Xueqing; (89 pag.)WO2018/116185; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 4549-33-1, 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 4549-33-1 as follows.

General procedure: Furanchalcone or quinoline (1 mmol), potassium hydroxide(1.5 mmol, 84.2 mg) and acetonitrile (10 mL), were placedin a 25 mL flat-bottomed flask equipped with a magneticstirring bar. The mixture was stirred and heated to reflux fora period of 5 min, under microwave irradiation. Then, 1,omega-dibromoalkane (1.1 mmol) was added to the reaction mixture,which was refluxed for 30 min (200 W). The crudereaction mixture was concentrated on a rotatory evaporatorand the residue was purified by column chromatographyover silica gel eluting with hexane and a mixture of hexaneethylacetate (9:1 ratio) to obtain bromoalkyl derivatives inyields ranging between 61 and 76%. Monitoring of thereaction progress and product purification was carried outby TLC.

According to the analysis of related databases, 4549-33-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Garcia, Elisa; Coa, Juan C.; Otero, Elver; Carda, Miguel; Velez, Ivan D.; Robledo, Sara M.; Cardona, Wilson I.; Medicinal Chemistry Research; vol. 27; 2; (2018); p. 497 – 511;,
Bromide – Wikipedia,
bromide – Wiktionary

945244-29-1, name is 5-Bromo-2-fluoro-4-methylaniline, 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. SDS of cas: 945244-29-1

Method B: To 4 necked round bottom flask, equipped with mechanical agitation, thermometer, and N2 inlet is added 5-bromo-2-fiuoro-4-methylaniline (200g, 0.98 mol), CH3COOK (192g, 1.95 mol, 2.0eq), bis(pinacolato)diboron (248g, 0.98 mol,1.0eq) and IPAC (3L). After degassing with N2 for 30 min, the mixture is warmed to 50C and Pd(dppf)Cl2 (8g, 4wt%) is added. The reaction mixture is heated under reflux for at least lOh until the content of starting material <2% (GC). The mixture is cooled to 20~30C, filtered through a pad of Celite and rinsed with IPAC (1L). The filtrate is concentrated to 400~500ml remaining. The residue is mixed with n-Heptane (700ml), filtered through a Si02 pad and eluted with IPAC/n-Heptane(l/5 first, ~2L, and then 2/5, ~3L ). The filtrate is concentrated to 350~400ml. n-Heptane (300ml) is added and the mixture is again concentrated to 350~400ml. The residue (suspension) is cooled to -10- -20C and filtered after stirring for 2- 5 h. The crude product is dissolved in MeOH (200 ml) at 30-40 C, then slowly add H20 (600 ml) dropwise in 0.5~lh. The suspension is cooled to 20-30 C and filtered after stirring for 1-2 h .The solid is dried under high vacuum to afford the title compound as off- white solid (183g, 74% yield and 99% purity detected by UV absorption at 210 nm; 1H NMR (400 MHz, CDC13): delta 7.42 (d, J = 10.2 Hz, 1H), 7.01 (d, J = 12.4 Hz, 1H), 3.76 (s, 2H), 2.64 (s, 3H), 1.55 (s, 12H); 13C NMR(500MHz,CDC13): delta 20.66, 20.67, 24.40, 82.93, 116.20, 124.37, 130.64, 135.02, (151.93, 153.37);19F NMR (400 MHz,CDC13): delta 145.72 The synthetic route of 945244-29-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ELI LILLY AND COMPANY; DECIPHERA PHARMACEUTICALS, LLC; ALLGEIER, Matthew Carl; FLYNN, Daniel L.; KAUFMAN, Michael D.; PATEL, Phenil J.; WOLFANGEL, Craig D.; WO2013/134243; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, 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 28342-75-8, Computed Properties of C6H2Br2F2

(3-3) Synthesis of Compound L3 (0072) Bis(triphenylphosphine)palladium(II) dichloride [Pd(PPh3)2Cl2](0.12 g, 0.17 mmol) and Compound L3-1 (1.5 g, 5.5 mmol) were placed in a reaction flask. Then, lithium chloride (1.4 g, 33.1 mmol), Compound L3-2 (6 g, 16.6 mmol), and 40 ml of anhydrous toluene were added to the reaction flask to obtain a mixture. The mixture was heated under reflux for 3 days. Next, the temperature of the mixture was slowly reduced to 20° C., and the mixture was filtered using celite to remove side products and to collect a filtrate. The solvents in the filtrate was removed, and then the filtrate was washed several times with ethyl acetate and with a saturated sodium chloride aqueous solution to collect an organic layer. The organic layer was dehydrated using sodium sulfate (Na2SO4) to obtain a crude product. The crude product was subjected to column chromatography (SiO2, ethyl acetate:n-hexane=1:3), followed by recrystallization in a mixed solvent having dichloromethane and n-hexane (dichloromethane:n-hexane=1:1) at 20° C., thereby obtaining transparent crystals (780 mg, 53percent yield). (0073) The spectrum analysis for the transparent crystals is: 1H NMR (400 MHz, d6-acetone): delta 8.84 (t, J=6.8 Hz, 1H), 8.74 (d, J=4.8 Hz, 2H), 7.947.87 (m, 4H), 7.417.38 (m, 2H), 7.29 (t, J=9.4 Hz, 1H); 19F NMR (376 MHz, d6-acetone, decouple H, 298 K): delta ?112.95. The transparent crystals were confirmed to be Compound L3 having a chemical structure represented by

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; NATIONAL TSING HUA UNIVERSITY; Chi, Yun; Tong, Bi-Hai; Duan, Tai-Nan; Ku, Hsiao-Yun; Chen, I-Jen; US9219237; (2015); B1;,
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. 876-53-9, name is 1,3-Dibromoadamantane, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H14Br2

General procedure: In a stainless-steelpressure microreactor of 17 mL capacity was charged5 wt % of catalyst FeHY (or NiHY), 100 mmol ofhaloadamantane (or halodiadamantane), and 400 mmolof dimethyl carbonate, the reactor was tightly closed,and the reaction mixture was heated for 5 h at 150.On completing the reaction, the reactor was cooled toroom temperature, opened, the reaction mixture wasfiltered through a layer of Al2O3. The unreacteddimethyl carbonate was distilled off

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 876-53-9.

Reference:
Article; Khusnutdinov; Shchadneva; Mayakova, Yu. Yu.; Russian Journal of Organic Chemistry; vol. 54; 11; (2018); p. 1728 – 1730; Zh. Org. Khim.; vol. 54; 9; (2018); p. 1710 – 1712,3;,
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. 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., SDS of cas: 2635-13-4

Benzo[1,3]dioxole-5-carbaldehyde (1.80 g, 11.96 mmol), 5-bromobenzo[1,3]dioxole (2.65 g, 13.16 mmol), and n-butyl lithium (5.26 ml, 13.16 mmol) were treated in the same manner as described above for the synthesis of (2,3-dihydrobenzo[1,4]dioxin-6-yl)-(3,5-dimethoxyphenyl)methanol. The crude material was purified via flash column chromatography (5% EtOAc in hexane gradient to 40% EtOAc in hexane in about 40 min.) to give bis-benzo[1,3]dioxol-5-yl-methanol as a light brown oil (2.69 g, 83%): 1H-NMR (CDCl3) 6.86-6.74 (m, 6H, Ar), 5.93 (s, 4H, 2CH2), 5.68 (d, J=3 Hz, 1H, CHOH), 2.16 (d, J=3 Hz, 1H, OH). The product was carried over to the next step.

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:
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3638-73-1, A common heterocyclic compound, 3638-73-1, name is 2,5-Dibromoaniline, molecular formula is C6H5Br2N, 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.

Sodium nitrite (65.2 mmol) was added in several portions to a solution of 2,5- dibromobenzenamine (55.8 mmol) in trifluoroacetic acid (80 mL) at 0 C. The resulting solution was added to a boiling solution of sodium sulfate (10 g) in 50% sulfuric acid (120 mL) and the reaction mixture was maintained at reflux for 1 h. Then the product was steam-distilled and the distillate was extracted with dichloromethane (2 x 200 mL). The combined organic layers were dried (sodium sulfate) and concentrated to provide 2,5-dibromophenol in 41% yield as a yellow solid.

The synthetic route of 3638-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2009/23844; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary