Category: 2468-56-6

Synthetic Route of 2468-56-6, A common heterocyclic compound, 2468-56-6, name is 6-Iodohex-1-yne, molecular formula is C6H9I, 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.

General procedure: 4.2.1 Synthesis of ethyl 2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)acetate (3a). To a solution of 2 (0.20 g, 0.99 mmol) in anhydrous DMF (3 mL) under N2 at 0 C was added NaH (0.044 g, 1.09 mmol). The mixture was warmed to rt and stirred for 30 min. After cooling back to 0 C, ethyl bromoacetate (0.12 mL, 1.09 mmol) was added and the mixture stirred at rt for 2 h. The reaction was quenched with saturated NH4Cl (10 mL) and the product extracted into ethyl acetate (3*30 mL). The combined organic extract was dried (Na2SO4) and the solvent removed in vacuo. Excess DMF was removed by Kugelrohr distillation. The crude product was purified by radial chromatography (hexane/ethyl acetate gradient) to give ester 3a (0.26 g, 93%) as a white solid.

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:
Article; Gibson, Sarah; Fernando, Rasika; Jacobs, Hollie K.; Gopalan, Aravamudan S.; Tetrahedron; vol. 71; 49; (2015); p. 9271 – 9281;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 2468-56-6, name is 6-Iodohex-1-yne, belongs to iodides-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 2468-56-6, Formula: C6H9I

To a solution of diisopropylamine (0.86 mL, 6.1 mmol) in anhydrous THF (10 mL) at 0 C was added n-butyllithium (2.5M in hexane) under nitrogen to give a light yellow solution which was stirred at room temperature for 10 mm. Ethyl 2-(1,3,5-trimethyl-1 H-pyrazol-4- yl)acetate (1.00 g, 5.10 mmol) was added at -78 C and the yellowish orange mixture was stirred at -78 C for 1 hr. 6-iodo-1-hexyne (0.78 mL, 5.9 mmol) was added to give orange mixture which was stirred at -78 C for another I hr before the addition of I ,3-Dimethyl- 3,4,5,6-tetrahydro-2(1 H)-pyrimidinone (DMPU). The mixture was slowly warmed to 0 C in 1 hr and water (5 mL) was added to quench the reaction. Ethyl acetate (3x 200 mL) was used to extract the product and the organic layer was washed with saturated aqueous ammonium chloride solution (20 mL), hydrochloric acid (IM, 20 mL), saturated aqueous sodium carbonate solution (20 mL), brine (20 mL), dried over MgSO4 and concentrated in vacuo to give an orange liquid. The crude product was purified by flash column chromatography by elution with 50% ethyl acetate in hexane to give Ethyl 2-(1 ,3,5-trimethyl-1 H-pyrazol-4-yl)oct- 7-ynoate as a pale yellow oil (233 mg, 17%). ESI HRMS, found 277.1919 (C16H25N202), MW, requires 277.1916. 1H NMR (COds, 400 MHz, 300 K) 64.12-4.01 (2H, m), 3.66 (3H, s), 3.37 (1H, dd, J = 8.4, 7.1 Hz,), 2.17 (6H, d, J = 3.8 Hz), 2.13 (2H, td, J = 7.1, 2.5 Hz), 2.07-1.97 (1 H, m), 1.89 (1 H, t, J 2.6 Hz), 1.73-1.64 (1 H, m), 1.54-1.46 (2H, m,), 1.35-1.27 (2H, m), 1.18 (3H, t, J= 7.1 Hz, Hk).

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, 6-Iodohex-1-yne, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IMPERIAL INNOVATIONS LIMITED; BELL, Andrew Simon; TATE, Edward William; LEATHERBARROW, Robin John; HUTTON, Jennie Ann; BRANNIGAN, James Antony; (213 pag.)WO2017/1812; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2468-56-6, name is 6-Iodohex-1-yne, belongs to iodides-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: 2468-56-6

To a stirred solution of iodo compound 20 (6.0 g, 28.84 mmol) in anhydrous DMF (30 mL) was added sodium azide (9.37 g, 144.20 mmol) at 0 C under argon atmosphere. The resulting mixture was stirred at rt for 3.5 h, then quenched with ice cold water (50 mL) and extracted with EtOAc (2 * 40 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentratedin vacuo. The crude residue was purified by silica gel column chromatography using 10% EtOAc/hexane to afford azide compound 21 (3.23 g, 91%) as a pale-yellow liquid. HRMS (ESI) m/z calcd for [C6H9N3+H]+: 124.0875, found 124.0218. 1H NMR (400 MHz, CDCl3): delta 3.31 (t, J = 6.7 Hz, 2H), 2.24 (td, J = 6.8, 2.5 Hz, 2H), 1.97 (t, J = 2.6 Hz, 1H), 1.77-1.70 (m, 2H), 1.65-1.58 (m, 2H). 13C NMR (100 MHz, CDCl3): 83.6, 68.9, 50.9, 27.8, 25.5, 18.0.

The synthetic route of 2468-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nagendra Reddy, Chintam; Grant, Gail E.; Ye, Qiuji; Powell, William S.; Patel, Pranav; Sivendran, Sashikala; Chourey, Shishir; Wang, Rui; Anumolu, Jaganmohan R.; Rokach, Joshua; Bioorganic and Medicinal Chemistry; vol. 25; 1; (2017); p. 116 – 125;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 2468-56-6,Some common heterocyclic compound, 2468-56-6, name is 6-Iodohex-1-yne, molecular formula is C6H9I, 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-Amino-oct-7-ynoic acid methyl ester hydrochloride was synthesised using the same methods previously reported for the synthesis of 2-Amino-pent-4-ynoic acid methyl ester hydrochloride (Kotha et al., Tetrahedron 2002, 58, 9203-9208). 1H NMR (300 MHz, D2O) delta 4.16 (t, 1H), delta 3.84 (s, 3H), delta 2.35 (t, 1H), delta 2.24 (m, 2H), delta 1.95 (m, 2H), delta 1.52 (m, 4H) ppm; 13C NMR (75 MHz, D2O) delta 170.9, 85.6, 69.6, 53.6, 52.9, 29.3, 27.0, 23.4, 17.3 ppm; HRMS (ESI) calcd for C9H15NO2 (M+) 170.1176, found 170.1171.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Iodohex-1-yne, its application will become more common.

Reference:
Patent; North Carolina State University; US2009/263438; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 2468-56-6, A common heterocyclic compound, 2468-56-6, name is 6-Iodohex-1-yne, molecular formula is C6H9I, 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.

General procedure: 4.2.1 Synthesis of ethyl 2-(3-(benzyloxy)-2-oxopyridin-1(2H)-yl)acetate (3a). To a solution of 2 (0.20 g, 0.99 mmol) in anhydrous DMF (3 mL) under N2 at 0 C was added NaH (0.044 g, 1.09 mmol). The mixture was warmed to rt and stirred for 30 min. After cooling back to 0 C, ethyl bromoacetate (0.12 mL, 1.09 mmol) was added and the mixture stirred at rt for 2 h. The reaction was quenched with saturated NH4Cl (10 mL) and the product extracted into ethyl acetate (3*30 mL). The combined organic extract was dried (Na2SO4) and the solvent removed in vacuo. Excess DMF was removed by Kugelrohr distillation. The crude product was purified by radial chromatography (hexane/ethyl acetate gradient) to give ester 3a (0.26 g, 93%) as a white solid.

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:
Article; Gibson, Sarah; Fernando, Rasika; Jacobs, Hollie K.; Gopalan, Aravamudan S.; Tetrahedron; vol. 71; 49; (2015); p. 9271 – 9281;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 2468-56-6, 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 2468-56-6 as follows.

3) Synthesis of 6-trifluoroacetamido-1-hexyne To a solution of sodium hydride (60% oil, 2.55 g, 63.6 mol) in DMF (50 ml), trifluoroacetamide (8.99 g, 79.6 mmol) was added portionwise as about 10 portions with ice cooling. Subsequently, a solution of 6-iodo-1-hexyne (3.31 g, 15.9 mmol) in DMF (15 ml) was added to the reaction mixture. The reaction mixture was stirred at room temperature for four hours. The reaction mixture was added with saturated aqueous ammonium chloride (100 ml) and ether (100 ml) for extraction. The ether layer was dried over magnesium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent; hexane-ethyl acetate mixed solvent) to afford 2.0 g of 6-trifluoroacetamido-1-hexyne (yield; 65.4%). Melting point: 41.0-42.5 C. 1H-NMR (270 MHz, CDCl3) delta ppm: 1.53-1.80 (m, 4H, -CH2(CH2)2-), 1.98 (t, 1H, J=2.7 Hz, H-CC-), 2.26 (dt, 2H, J=2.5, 6.7 Hz, CC-CH2-), 3.41 (q, 2H, J=6.8 Hz, CH2-N), 6.48 (brs, 1H, NHTfa)

According to the analysis of related databases, 2468-56-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Institute of Physical and Chemical Research; US6265569; (2001); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 2468-56-6, name is 6-Iodohex-1-yne, belongs to iodides-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 2468-56-6, Product Details of 2468-56-6

A mixture of 4,4?-bipyridine (1.0 g, 6.4 mmol) and 6-iodo-1-hexyne (4.6 g, 22 mmol)in dry MeCN (30 mL) was heated at 105 oC / 6 psi under N2 for 3 h. The reaction mixture was cooled to room temperature and the resulting reddish precipitate was filtered and washed thoroughly with MeCN. The solid was dissolved in H2O (100 mL), followed by the addition of excess of NH4PF6, resulting in the precipitation of an off-white solid which was collected by centrifugation, washed with H2O (3 × 20 mL), MeOH (1 × 20 mL) and dried in vacuo to yield HV?2PF6 as a light brown solid (2.4 g) in 62% yield

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodohex-1-yne, and friends who are interested can also refer to it.

Electric Literature of 2468-56-6,Some common heterocyclic compound, 2468-56-6, name is 6-Iodohex-1-yne, molecular formula is C6H9I, 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.

General procedure: Concentrated sulfuric acid (0.15 mL) was added under stirring at ambient temperature to a suspension of 25 mmole of uracil 3 or uracil derivatives, namely 6-methyluracil 4, thymine 5, quinazoline-2,4(1H,3H)-dione 6 and hexamethyldisilazane (HMDS, 62.5 mmol) in 100 mL of toluene. The mixture was refluxed for 4 h, the solvent and excessive HMDS were removed to afford bis(trimethylsilyl) ether derivative 7. This crude product was engaged in the next step without any previous purification. A solution of 40 mmole of appropriate alkyne (propargyl bromide, 5-iodo-1-pentyne, 6-iodo-1-hexyne) in DMF (3 mL) was added to the crude product 7 and the reaction mixture was stirred at 115-130 C for 12 h. After the solvent was distilled off under reduced pressure, 200 ml of chloroform was added to the residue, and the mixture was filtered. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel using as eluent first petroleum ether, then petroleum ether-ethyl acetate (1.5:1) and then ethyl acetate. From the third fraction the target N1-alkynyl-3,4-dihydro-2,4-dioxopyrimidines (3a,b, 4b,c, 5a,b, 6a,b) were isolated.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Iodohex-1-yne, its application will become more common.

These common heterocyclic compound, 2468-56-6, name is 6-Iodohex-1-yne, 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. COA of Formula: C6H9I

General procedure: A mixture of the corresponding precursor (1 eq) and alkylating agent (1.5 eq) and K2CO3 (2.5 eq) in DMF was stirred at rt till completion of the reaction. H2O was added and the mixture was extracted with EtOAc. The organic layer was dried, filtered and evaporated. The crude compound was used in next reaction step without further purification (it can be impure with the corresponding precursor).

The synthetic route of 6-Iodohex-1-yne has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fundacion del Sector Publico Estatal Centro Nacional de Investigaciones Oncologicas Carlos III (F.S.P. CNIO); PASTOR FERNANDEZ, Joaquin Angel; BLASCO MARHUENDA, Maria Antonia; MARTINEZ GONZALEZ, Sonia; BLANCO-APARICIO, Carmen; GARCIA GARCIA, Ana Belen; VARELA BUSTO, Carmen; GOMEZ-CASERO ESTEBAN, Elena; BEJARANO BOSQUE, Leire; MENDEZ PERTUZ, Marinela; MARTINEZ RODRIGUEZ, Paula; GARCIA-BECCARIA, Maria; (71 pag.)EP3623370; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 2468-56-6, 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. 2468-56-6 name is 6-Iodohex-1-yne, 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.

General procedure: Concentrated sulfuric acid (0.15 mL) was added under stirring at ambient temperature to a suspension of 25 mmole of uracil 3 or uracil derivatives, namely 6-methyluracil 4, thymine 5, quinazoline-2,4(1H,3H)-dione 6 and hexamethyldisilazane (HMDS, 62.5 mmol) in 100 mL of toluene. The mixture was refluxed for 4 h, the solvent and excessive HMDS were removed to afford bis(trimethylsilyl) ether derivative 7. This crude product was engaged in the next step without any previous purification. A solution of 40 mmole of appropriate alkyne (propargyl bromide, 5-iodo-1-pentyne, 6-iodo-1-hexyne) in DMF (3 mL) was added to the crude product 7 and the reaction mixture was stirred at 115-130 C for 12 h. After the solvent was distilled off under reduced pressure, 200 ml of chloroform was added to the residue, and the mixture was filtered. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel using as eluent first petroleum ether, then petroleum ether-ethyl acetate (1.5:1) and then ethyl acetate. From the third fraction the target N1-alkynyl-3,4-dihydro-2,4-dioxopyrimidines (3a,b, 4b,c, 5a,b, 6a,b) were isolated.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodohex-1-yne, and friends who are interested can also refer to it.

Reference:
Article; Andreeva, Olga V.; Belenok, Maya G.; Saifina, Liliya F.; Shulaeva, Marina M.; Dobrynin, Alexey B.; Sharipova, Radmila R.; Voloshina, Alexandra D.; Saifina, Alina F.; Gubaidullin, Aidar T.; Khairutdinov, Bulat I.; Zuev, Yuriy F.; Semenov, Vyacheslav E.; Kataev, Vladimir E.; Tetrahedron Letters; vol. 60; 47; (2019);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com