Tag: M.W=100-200

Synthetic Route of 626-88-0, These common heterocyclic compound, 626-88-0, name is 1-Bromo-4-methylpentane, 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.

37.1 2-[(tert-butoxycarbonyl)amino]-6-methylheptanoic acid A solution of diisopropylamine (13.2 ml; 0.094 mol) in 130 ml of tetrahydrofuran (THF) is cooled down to -40 C. n-butyllithium (37 ml of a 2.5 M solution in hexane; 0.094 mol) is added dropwise. The temperature is allowed to rise to 0 C. At this temperature, Boc-glycine (5 g; 0.028 mol) in solution in 30 ml of THF is introduced into the mixture. The reaction medium is left for ten minutes at this temperature then 1-bromo-4-methylpentane (7.9 ml; 0.056 mol) in solution in 20 ml of THF is added rapidly. The temperature is allowed to return to 23 C. and the mixture is stirred at this temperature for one hour. After hydrolysis with 100 ml of water then acidification with 150 ml of a saturated solution of potassium hydrogen sulphate, the mixture obtained is extracted twice with 50 ml of ethyl acetate. The organic phase is washed with 100 ml of water then with 100 ml of a saturated solution of sodium chloride. After drying over magnesium sulphate and evaporating the solvent, the residue obtained is purified on a silica column (eluent: ethyl acetate-heptane/6-4) in order to produce a white-coloured powder with a yield of 50%.

The synthetic route of 626-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chabrier De Lassauniere, Pierre-Etienne; Harnett, Jermiah; Bigg, Dennis; Liberatore, Ann-Marie; Pommier, Jacques; Lannoy, Jacques; Thurieau, Christophe; Dong, Zheng Xin; US2005/38087; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 452-63-1, name is 1-Bromo-4-fluoro-2-methylbenzene, 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 452-63-1, HPLC of Formula: C7H6BrF

1. Preparation of 2-[6-(3-Amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl]-4-fluoro-benzonitrile and Pharmaceutically Acceptable Salts A mixture of 2-bromo-5fluorotoluene (2) (3.5 g, 18.5 mmol) and CuCN (2 g, 22 mmol) in DMF (100 mL) was refluxed for 24 hours. The reaction was diluted with water and extracted with hexane. The organics were dried over MgSO4 and the solvent removed to give product 3 (yield 60%). 1H-NMR (400 MHz, CDCl3): delta 7.60 (dd, J=5.6, 8.8 Hz, 1H), 6.93-7.06 (m, 2H), 2.55 (s, 3H).

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-4-fluoro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Christopher, Ronald J.; Covington, Paul; US2007/60530; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1073-06-9, name is 1-Bromo-3-fluorobenzene, 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 1073-06-9, Formula: C6H4BrF

Diacetoxypalladium (3.3 mg, 0.01 mmol) was added to a stirred mixture of methyl 2-morpholino-4-oxo-8-[(2R)-pyrrolidin-2-yl]chromene-6-carboxylate (121 mg, 0.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (16.61 mg, 0.03 mmol), 1-bromo-3-fluorobenzene (0.047 mL, 0.42 mmol) and cesium carbonate (165 mg, 0.51 mmol) suspended in 1,4-dioxane (3.3 mL). The resulting suspension was degassed with argon and then stirred at 100 C. for 20 h. The reaction mixture was allowed to cool to room temperature, and the crude product was purified by flash chromatography on silica gel eluting with 0 to 7% propanol in DCM. The solvent was evaporated to dryness to afford methyl 8-[(2R)-(1-(3-fluorophenyl)pyrrolidin-2-yl)]-2-morpholino-4-oxo-4H-chromene-6-carboxylate (120 mg, 79%) as a yellow oil which solidified on standing. Mass Spectrum: m/z [M+H]+=453.

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-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; US2012/264731; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 399-94-0, A common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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.

Description 14:; 2-Bromo-3,6-difluorobenzaldehyde (D14)To solution of diisopropylamine (13.29 mL, 93 mmol) in THF (300 mL) at -78 0C, was added n-butyllithium (34.2 mL of 2.5M in hexanes, 85 mmol), dropwise over 10 mins. The mixture was stirred at -78 0C for 15 mins and then 2-bromo-1 ,4-difluorobenzene (15 g, 78 mmol) in THF (100 mL) was added dropwise over 15 mins maintaining the temperature below -65 C. After stirring for 1 hr at -78 0C, N,N-dimethylformamide (6.62 mL, 85 mmol) was added via syringe. The mixture was stirred at -78 0C for 30 mins and then quenched with sat. NH4CI solution and the mixture was allowed to reach room temperature. The product was extracted into ether and the extracts were dried (Na2SO4) and evaporated. Chromatography (silica, 0-100% dichloromethane in hexane) gave the title compound(D14) as a yellow solid (12.73 g)NMR (deltaH), (CDCI3): 7.16 (1 H, m), 7.35 (1 H, m), 10.32 (1 H, s).

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/107455; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 57951-72-1, name is 1-Bromo-2-cyclopropylethyne, molecular formula is C5H5Br, 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. SDS of cas: 57951-72-1

To a solution of (bromoethynyl)cyclopropane (60 g, 414 mmol) in piperidine (345 ml) at 0 C. was added ethynyltrimethylsilane (44.7 g, 455 mmol) and CuI (7.88 g, 41.4 mmol). The solution was then stirred at rt for 2 hours. The reaction was quenched by adding sat. aq. NH4Cl solution and then extracted with TBME. The organic layer was washed with water, brine, dried over MgSO4 and concentrated. The crude material was purified by silica gel column chromatography, heptane as eluant to give product (42 g, 62% yield). 1H NMR (400 MHz, CDCl3) 0.13-0.24 (m, 9H) 0.72-0.91 (m, 4H) 1.25-1.36 (m, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57951-72-1, its application will become more common.

Reference:
Patent; Novartis AG; FU, Jiping; JIN, Xianming; KARUR, Subramanian; LAPOINTE, Guillaume; MADERA, Ann Marie; SWEENEY, Zachary Kevin; (45 pag.)US2016/166548; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 74586-53-1, 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. 74586-53-1 name is 3-Bromo-5-methylaniline, 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.

Dioxane (720 mL) in a 1 L three-necked round bottom flask was degassed for 30 minutes. 3-Bromo-5-methylaniline (60 g, 193 mmol), (bispinacolato)diboron (96 g, 377 mmol), potassium acetate (42.7 g, 435 mmol), X-Phos (8.3 g, 17.41 mmol) and tris(dibenzylideneacetone)dipalladium(0) (3.99 g, 4.35 mmol) were added to the degassed solvent. After stirring for 10 minutes at room temperature, the reaction was heated to an internal temperature of 80 C. After 4 hours, the heating mantle was removed and replaced with an ice water bath. The reaction mixture was cooled to 30 C, and was then filtered through a pad of CELITE (washing with 500 mL of methyl tert-butyl ether). This was transferred to a 4 L seperatory funnel containing 500 mL pH 8 phosphate buffer, 500 mL brine, and an additional 500 mL of methyl tert-butyl ether. The layers were cut and the organic washed with 1 L of a 1 : 1 mixture of brine and water. The aqueous layers combined and were sequentially back extracted with a second 500 mL portion of methyl tert-butyl ether. The combined organics were treated with 100 g of magnesium sulfate and the resulting mixture stirred for 20 minutes. This was then filtered and concentrated under reduced pressure. The resultant residue was purified by flash chromatography (0-25% ethyl acetate in hexanes) to yield 3-methyl-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)aniline as a light orange solid. MS ESI calc’d. for C 3H21B O2 [M + H]+ 234, found 234.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ANTHONY, Neville, J.; ANDRESEN, Brian, M.; NORTHRUP, Alan, B.; CHILDERS, Kaleen, K.; DONOFRIO, Anthony; MILLER, Thomas, A.; LIU, Yuan; MACHACEK, Michelle, R.; WOO, Hyun Chong; SPENCER, Kerrie, B.; ELLIS, John Michael; ALTMAN, Michael, D.; ROMEO, Eric, T.; GUAY, Daniel; GRIMM, Jonathan; LEBRUN, Marie-Eve; ROBICHAUD, Joel, S.; WANG, Liping; DUBOIS, Byron; DENG, Qiaolin; WO2014/176210; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1647-26-3, 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.

(a) 2-(8-Cyclohexyloctyl)-benzaldehyde To an ice cold solution of 1-hexyne (49.6 mmoles) in freshly distilled tetrahydrofuran (50 ml) containing a trace of triphenylmethane was added dropwise n-butyl lithium in hexane (49.5 mmoles). About 10 minutes after the addition was stopped, sieve dried hexamethylphosphoramide (57.5 mmoles) was added and the solution stirred for 10 minutes. A solution of 2-cyclohexylethyl bromide (51.3 mmoles) in tetrahydrofuran (10 ml) was added and the reaction mixture was stirred for about 3 hours as the temperature rose to room temperature. The mixture was taken up in ether (100 ml) and washed with water (3*100 ml) and sodium chloride solution (100 ml). The organic phase was dried over magnesium sulfate and evaporated to leave an oil which was purified by flash chromatography to give 1-cyclohexyloct-3-yne.

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; SmithKline Beckman Corporation; US4730005; (1988); 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. 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, A new synthetic method of this compound is introduced below., Product Details of 202865-83-6

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), Na2CO3 (54 mg, 0.51 mmol) in degassed 1,4-dioxane and H2O (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 oC under microwave radiation for 45 minutes.1 N HCl (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 HPLC-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. [389] 1H NMR (500 MHz, DMSO) delta 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 (s, 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 (s, 3H), 2.31 (s, 3H), 1.24 (d, J = 6.7 Hz, 6H); MS (m/z): 536.0 [M+H]+.

The synthetic route of 202865-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M., Arshad; CIBLAT, Stephane; DERY, Martin; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu; SRIVASTAVA, Sanjay; SHIPPS, Gerald, W.; COOPER, Alan, B.; BRUNEAU-LATOUR, Nicolas; LY, Vu, Linh; (314 pag.)WO2016/196644; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 452-63-1, 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. 452-63-1 name is 1-Bromo-4-fluoro-2-methylbenzene, 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.

To a solution of bis (dibenzylidene acetone) palladium (0) (0.719 g, 1.25 mmol) and tris (2-methylphenyl) phosphine (0. 761 g, 2. 50 mmol) in toluene (150 mL) were added sodium tert- butoxide (3. 36 g, 35.0 mmol), 2-BROMO-5-FLUOROTOLUENE (3.16 mL, 25.0 mmol) and tert-butyl 1-piperazinecarboxylate (5.03 g, 27.0 mmol) at room temperature, and the mixture was stirred under a nitrogen atmosphere at 100C for 20 hrs. After cooling, the reaction mixture was washed with water and saturated brine, dried (MGS04) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate = 9/1) to give the title compound as a yellow oil (2.50 g, yield 34%). 1H NMR (300 MHz, CDC13) 8 PPM : 1.49 (s, 9 H), 2.30 (s, 3 H), 2.77-2. 80 (m, 4 H), 3.54-3. 57 (m, 4 H), 6.80-6. 96 (m, 3 H). LC/MS (ESI) m/z 295 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-fluoro-2-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; WO2004/46107; (2004); A1;,
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. 53078-85-6, name is 2-Bromo-5-methylaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5-methylaniline

A mixture of compound 36b (3 3 g, 17 7 mmol), glycerin (3 3 g, 35 5 mmol), nitrobenzene (2 2 g, 17 7 mmol) and 75% aqueous sulfuric acid (10 mL, 138 mmol) is stirred at 15O0C for 3 h (mixture turns black and viscous) The reaction mixture is cooled down, poured into ice-water (200 mL) and 10 N aqueous NaOH is added (30 mL, 300 mmol) The black mixture is then shaken with EtOAc (100 mL) and is centrifuged in 50 mL portions The upper EtOAc layers are combined and the bottom aqueous layers containing the black tar are shaken with EtOAc and re-cent?fuged All EtOAc extracts are combined, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 4.8 g of a brown-red oil. This material is chromatographed on 80 g silica gel column (CombiFlash Companion apparatus, hexanes/EtOAc gradient). The fractions containing the compound are concentrated under vacuum to afford compound 36c as a white solid (3.26 g, 83% yield).

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; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; CARSON, Rebekah J.; FADER, Lee; KAWAI, Stephen; LANDRY, Serge; WO2009/62288; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary