Category: 4549-33-1

Synthetic Route of 4549-33-1,Some common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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.

1,9-Dibromononane (610 muL, 3 mmol) was added to a stirred solution of the product of Preparation 1 (377 mg, 1 mmol) and DIPEA (1.05 mL, 6 mmol) in DMF (5 mL) at 50 C. The reaction mixture was heated at 80 C. for 72 h and then the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (10% MeOH in DCM containing 0.5% NH4OH) to give the title compound (292 mg, 0.5 mmol, 50%).

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mammen, Mathai; Hughes, Adam; US2004/242622; (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. 4549-33-1, name is 1,9-Dibromononane, A new synthetic method of this compound is introduced below., Computed Properties of C9H18Br2

Example 25 (n=9); (a) 1, 1′- [ (Nonane-l,-9-diyl) dioxylbis [ (11S, llaS)-10- (tert- butyloxycarbonyl)-7-methoxy-11-(tetrahydro-pyran-2-yloxy)-2- methylidene-1, 2, 3, 10, 11, 11a-hexahydro-5H-pyrrolo [2, 1- c] f, 4Jbenzodiazepine-5-one] (28b); 1,9-Dibromononane (35.75 mg, 0.125 mmol, 0.5 equiv. ) was added to the mixture of monomer 27 (115 mg, 0.25 mmol, 1.0 equiv. ), potassium carbonate (53 mg, 0.50 mmol, 2.0 equiv. ) and a catalytic amount of potassium iodide (1 mg) in dry DMF (30 mL), and the resulting mixture was heated to 90 C under a nitrogen atmosphere for 5 h. Removal of excess solvent under reduced pressure afforded a crude solid, which was subjected to flash column chromatography (Si02, 50% EtOAc-hexane) to afford the dimerized compound 28b (89 mg, 0.085 mmol, 68% yield, mixture of diastereomers from THP protecting group) as a solid: [alpha]29D = +36 (c = 0. 11, CHCl3) ; 1H NMR (CDC13, 400 MHz): No. 1.25-1. 67 (m, 72H, 14-H, 15-H, 16-H, Boc, THP), 1.70-1. 91 (m, 16H, 13-H, THP), 2. 51-2.58 (m, 2H, 1-H), 2.72-2. 81 (m, 2H, 1-H), 2.84-2. 97 (m, 4H, 1-H), 3.51-3. 65 (m, 8H, lla-H, THP), 3. 85-4. 19 (m, 28H, 3-H, 12-H, 7-OMe, THP), 4.26-4. 38 (m, 4H, 3-H), 5.00-5. 18 (m, 12H, 2a-H, THP), 5.65-5. 74 (d, 2H, 11-H), 5.76-5. 88 (d, 2H, 11-H), 6.49 (s, 2H, 9-H), 6.85 (s, 2H, 9-H), 7.16 (s, 2H, 6-H), 7.19 (s, 2H, 6-H) ; 13C NMR (CDCl3, 100 MHz) : No. 20.2, 25.2, 25.9, 28.1, 28.2, 29.0, 29.3, 29.4, 31.0, 31. 1,35. 1,35. 4, 50.6, 56.1, 59.9, 60.0, 63.5, 68.9, 69.2, 91.1, 96.2, 100.3, 109.3, 110.4, 110.5, 114.8, 114. 9,129. 8,142. 1,148. 6,148. 9, 167.2 ; IR (neat): 2935,2856, 1704,1645, 1604,1511, 1454,1430, 1401,1367, 1325,1255, 1210,1163, 1119, 1020,907, 729 cm~1 ; MS (ES+) m/z (relative intensity) 1068 ([M + Na]+., 13), 1045 ( [M + H]+., 100), 1046 ([M + 2H] +-, 65), 943 (42), 843 (28).

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; SPIROGEN LIMITED; WO2005/85259; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application 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.

DIEA (259 mg, 2 mmol) and 1,9-dibromoctane (286 mg,1 mmol) were added to the mixture whichincluded compound 1a (508 mg, 2 mmol) in toluene/ethanol (EtOH) (1:1) (60 mL), followed by refluxfor 48 h. The solvent was removed under vacuum. The process of this reaction was controlled byLC-MS and TLC. For TLC control and purification, the DCM/MeOH (7/1) system was used. Neutralalumina oxide was used to purify the product (yield 50%). LC-MS: [M + H]+ = 633. 1H NMR (500 MHz, MeOD): delta = 1.31(m, 2H, CH2), 1.41 (m, 12H, 6xCH2), 2.20 (m, 4H, 2xCH2),3.04 (m, 4H, 2xNHCH2), 3.13 (m, 4H, 2xNHCH2), 3.89 (d, J = 10.3 Hz, 4H, 2xNCH2) 7.86 (t, J = 7.8 Hz,4H, ArH), 8.41 (d, J = 8.1 Hz, 4H, ArH), 8.60 (d, J = 7.1 Hz, 4H, ArH) ppm.13C NMR (125 MHz, CDCl3): delta = 22.3 (CH2), 23,2 (CH2), 26,5 (CH2), 27,1 (CH2), 28.7 (CH2),37.9 (CH2), 46.5 (CH2), 48,6 (CH2), 122.3 (Caro), 127.2 (CaroH), 127.3 (Caro), 130.7 (CaroH), 131.3 (Caro),134.3 (CaroH), 163.5 (C=O) ppm.

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; Keskin, Elif; Ucisik, Mehmet Hikmet; Sucu, Bilgesu Onur; Guzel, Mustafa; Molecules; vol. 24; 24; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 4549-33-1, 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. 4549-33-1, name is 1,9-Dibromononane, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6-(4-chlorophenyl)-1-methyl-8-(1H-pyrazol-4- yl)spiro[benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine-4,1′-cyclopropane] (59-2) (100 mg, 249 mumol) in DMF(1.5 mL) was added Cs2CO3 (121 mg, 373 mumol) and 1,9-dibromononane (85.2 mg, 298 mumol) . The mixture was stirred for 4h at 30 C. Water(30 mL) and EA(30 mL*2) were added. The Combined organic layers was dried over Na2SO4 and concentrated, purified with prep- TLC (EA=100%) to give 8-(1-(9-bromononyl)-1H-pyrazol-4-yl)-6-(4-chlorophenyl)-1- methylspiro[benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine-4,1′-cyclopropane] (113-1) (39.2 mg, 26.1 %) as an oil. LCMS (ES+): m/z= 605 [M + H]+

The chemical industry reduces the impact on the environment during synthesis 1,9-Dibromononane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; FITZGERALD, Mark, E.; MICHAEL, Ryan, E.; (790 pag.)WO2017/197056; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 4549-33-1, A common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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.

Synthesis of Compound 9.1 [0189] To a solution of 2075-45-8 (1.30 g, 8.84 mmol, 1.0 eq) in CH3CN (20 ml) were added K2C03 (1.41 g, 13.26 mmol, 1.5 eq) and 4549-33-1 (5.05 g, 7.68 mmol, 2.0 eq). The reaction mixture was stirred at 65 C for 16 h. After cooling down to ambient temperature, the resulting solution was diluted with H20 (100 mL), extracted with ethyl acetate (100 ml). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by silica gel column (PE / EA = 10 / 1) to give 9.1 (2.08 g, yield: 66%) as a white solid. 1H NMR (400 MHz, CDC13) delta: 7.44 (s, 1H), 7.38 (s, 1H), 4.09 (t, J = 1.2 Hz, 2H), 3.41 (t, J = 1.2 Hz, 2H), 1.87-1.80 (m, 4H), 1.42-1.37 (m, 2H), 1.29-1.24 (m, 8H); ESI-MS (M+H) +: 351.0.

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC.; JENKINS, Tracy; VESSELS, Jeffery; WO2014/143672; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 4549-33-1, These common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, 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.

2,2, 12, 12-Tetramethyltridecanedioic acid diethyl ester (153).; Under N2 atmosphere and at-78 C, a solution of lithium diisopropylamide (2 M in heptane/THF/ethylbenzene, 52.5 mL, 105 mmol) was added dropwise to a solution of ethyl isobutyrate (17.4 g, 150 mmol) in THF (50 mL). The mixture was stirred for 1 h and 1, 9-dibromononane (151, 14.3 g, 50 mmol) was added, followed by DMPU (4.4 g, 34.3 mmol). The mixture was stirred for 30 min and the cooling bath was removed. After 30 min, the THF was evaporated under reduced pressure. The residue was diluted with saturated NH4CI ‘bluti6’n” (300 mL) aSd’-exti’Scted with ethyl acetate (3 x l00 mL). The combined organic layers was washed with brine (200 mL), 5 % aqueous HC1 (100 mL) and saturated NaHC03 solution (50 mL), and dried over Na2S04. The solvent was removed under reduced pressure and the residue was distilled in high vacuo to give 153 (14.0 g, 79 %) as an oil. Bp 150-151 C/0. 1 mmHg. 1H NMR (CDC13) : 8 (ppm): 4.08 (q, J= 7. 2, 4 H), 1.48-0. 98 (m, 18 H), 1.21 (t, J= 7.2, 6 H), 1.12 (s, 12 H). 13C NMR (CDCl3) : 5 (ppm) : 178.1, 60.0, 42.1, 40.7, 30.0, 29.4, 25.1, 24. 8, 14.2.

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ESPERION THERAPEUTICS, INC.; WO2005/68410; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 4549-33-1, 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. 4549-33-1, name is 1,9-Dibromononane, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of SA (15 mg, 0.06 mmol) in DMF (1 mL, freshly distilled from CaH2), was added K2CO3 (25 mg, 0.18 mmol), followed by the addition of dibromoalkane (0.24 mmol). The obtained mixture was then stirred under N2 atmosphere at 50 C for 12 h. Afterwards, the reaction mixture was cooled to room temperature and quenched by brine (5 mL). The mixture was then extracted with DCM(5 mL x 3), washed successively with brine (10 mL x 3) and water (10 mL x 3), dried over Na2SO4,filtered, and concentrated in vacuo. The residue was purified by silica gel CC (EtOAc/PE ranged from 5:95 to 10:90 depending on the TLC analysis) to yield 15-20.

The chemical industry reduces the impact on the environment during synthesis 1,9-Dibromononane. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jun; Ling, Wei; Yang, Zhiqiang; Liang, Yan; Zhang, Linyan; Guo, Can; Wang, Kailing; Zhong, Balian; Xu, Shihai; Xu, Ying; Marine Drugs; vol. 17; 2; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4549-33-1, name is 1,9-Dibromononane, molecular formula is C9H18Br2, 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. HPLC of Formula: C9H18Br2

2,2,12,12-Tetramethyltridecanedioic acid diethyl ester (153). Under N2 atmosphere and at -78 C., a solution of lithium diisopropylamide (2 M in heptane/THF/ethylbenzene, 52.5 mL, 105 mmol) was added dropwise to a solution of ethyl isobutyrate (17.4 g, 150 mmol) in THF (50 mL). The mixture was stirred for 1 h and 1,9-dibromononane (151, 14.3 g, 50 mmol) was added, followed by DMPU (4.4 g, 34.3 mmol). The mixture was stirred for 30 min and the cooling bath was removed. After 30 min, the THF was evaporated under reduced pressure. The residue was diluted with saturated NH4Cl solution (300 mL) and extracted with ethyl acetate (3*100 mL). The combined organic layers was washed with brine (200 mL), 5% aqueous HCl (100 mL) and saturated NaHCO3 solution (50 mL), and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was distilled in high vacuo to give 153 (14.0 g, 79%) as an oil. Bp 150-151 C./0.1 mmHg. 1H NMR (CDCl3): delta (ppm): 4.08 (q, J=7.2, 4H), 1.48-0.98 (m, 18H), 1.21 (t, J=7.2, 6H), 1.12 (s, 12H). 13C NMR (CDCl3): delta (ppm): 178.1, 60.0, 42.1, 40.7, 30.0, 29.4, 25.1, 24.8, 14.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4549-33-1, its application will become more common.

Reference:
Patent; Dasseux, Jean-Louis Henri; Oniciu, Carmen Daniela; US2004/192771; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 4549-33-1, 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. 4549-33-1 name is 1,9-Dibromononane, 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 stirred solution of mixture of 3,7-bis(tert-butoxycarbonylamino)-2,8-dimethyl-5- phenylphenazin-5-ium chloride and 3,7-bis(tert-butoxycarbonylamino)-2,6-dimethyl-5- phenylphenazin-5-ium chloride (500 mg, 0.909 mmol) in 10 mL of DMF was added cesium carbonate (738 mg, 2.27 mmol) and stirred at RT for 15 min. The reaction mixture was cooled to 0C and 1,9-dibromononane (156 mg, 0.545 mmol, diluted with 1 mL of DMF) was added dropwise. The reaction mixture was stirred at RT for 12 h. The reaction was monitored by TLC and LCMS. After completion of reaction, the mixture was diluted with ice-cold water and filtered. The solid residue obtained after filtration was dissolved in diethyl ether (200 mL) and washed with brine solution (3×50 mL). The ether layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford the crude product which was purified by column chromatography (neutral alumina, eluent 0-20% EtOAc in hexane) to afford the desired product (mixture of 2 products of same mass) as a dark brown solid (400 mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,9-Dibromononane, and friends who are interested can also refer to it.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; PHAM, Son Minh; HART, Barry Patrick; (437 pag.)WO2017/19832; (2017); 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. 4549-33-1, name is 1,9-Dibromononane, A new synthetic method of this compound is introduced below., Quality Control of 1,9-Dibromononane

General procedure: The synthesis of p-aminophenoxy alkanes was accomplished intwo steps, as shown in Fig. 1. In the first step various p-nitrophenoxyalkanes were synthesized according to the given procedure [28]. Finely powdered anhydrous potassium carbonate (7.86 g,57 mmol) was added to a solution of p-nitrophenol (8.0 g, 57 mmol) in DMF (50 mL) and toluene (30 mL). The reaction mixture was stirred at room temperature for 1 h under an inert atmosphere of nitrogen. Afterwards, dropwise addition of the corresponding dibromoalkane (28.5 mmol) was made over a period of 30 min andthe mixture was maintained at 120 C for 12 h. The conversion of reactants into the product was monitored by TLC (n-hexane: ethylacetate 1:4). After the complete consumption of reactants, the reaction mixture was cooled to room temperature and then precipitated in distilled water, filtered and recrystallized from ethanol. In the second step, 10% Pd/C (0.03 g) was added in solution of p-nitrophenoxy p-nitrophenoxyalkanes (4 mmol) in 90 mL of ethanol followed by the dropwise addition of hydrazinium monohydrate (3.8 mL) to the reaction mixture over a period of 1 h. The reaction mixture was refluxed for 3 h after which the catalyst was filtered off. The p-aminophenoxyalkanes (D3,D5,D9,D10 and D11) were obtained byprecipitation in distilled water, followed by drying and recrystallization in the smallest possible volume of ethanol [29].

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Iqbal, Asma; Siddiqi, Humaira Masood; Akhter, Zareen; Qaiser Fatmi, Muhammad; Journal of Molecular Structure; vol. 1151; (2018); p. 135 – 141;,
Bromide – Wikipedia,
bromide – Wiktionary