Category: 116986-09-5

Electric Literature of 116986-09-5 ,Some common heterocyclic compound, 116986-09-5, molecular formula is C8H8BrNO2, 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.

A mixture of 2-hydroxyl-5-methoxybenzaldehyde (leq) and methyl 3-(bromomethyl)picolinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) (1.2eq) was added to this mixture and the reaction was stirred at room temperature for 8-10 hours. The solvent was then evaporated and the reaction mixture extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The crude product was purified using S1O2 column chromatography and eluted with the solvent system EtOAc: hexanes = 3:2 to obtain pure product as pale yellow powder with a yield of 82%. IR (Diamond, cm-1): 2897, 1712, 1671, 1607, 1567, 1490, 1445, 1398, 1365, 1275, 1232, 1 165, 1 139, 1 106; 1H-NMR (400 MHz, DMSO-d6): d 10.35 (s, 1H), 8.65 (dd, J = 4.6, 1.28 Hz, 1H), 8.2 (dd, J = 7.84, 0.76 Hz, 1H), 7.66 (dd, J= 7.88, 4.68 Hz, 1H), 7.24 (m, 3H), 5.49 (s, 2H), 3.83 (s, 3H), 3.77(s, 3H); 13C-NMR (100 MHz, DMSO-d6): d 188.81, 166.12, 154.66, 153.55, 148.49, 146.69, 136.89, 133.04, 126.43, 124.89, 122.96, 1 15.79, 1 10.68, 67.44, 55.56, 52.34. MS (ESI) m/z found 324.08 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 98% pure.

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. 116986-09-5, Methyl 3-(bromomethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; THE CHILDREN’S HOSPITAL OF PHILADELPHIA; SAFO, Martin, K.; ZHANG, Yan; PARAGE, Piyusha, Pradeep; XU, Guoyan; GHATGE, Mohini; VENITZ, Jurgen; ABDULMALIK, Osheiza; (78 pag.)WO2019/182938; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116986-09-5 ,Some common heterocyclic compound, 116986-09-5, molecular formula is C8H8BrNO2, 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.

A mixture of 2-hydroxyl-5-methoxybenzaldehyde (leq) and methyl 3-(bromomethyl)picolinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) (1.2eq) was added to this mixture and the reaction was stirred at room temperature for 8-10 hours. The solvent was then evaporated and the reaction mixture extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The crude product was purified using S1O2 column chromatography and eluted with the solvent system EtOAc: hexanes = 3:2 to obtain pure product as pale yellow powder with a yield of 82%. IR (Diamond, cm-1): 2897, 1712, 1671, 1607, 1567, 1490, 1445, 1398, 1365, 1275, 1232, 1 165, 1 139, 1 106; 1H-NMR (400 MHz, DMSO-d6): d 10.35 (s, 1H), 8.65 (dd, J = 4.6, 1.28 Hz, 1H), 8.2 (dd, J = 7.84, 0.76 Hz, 1H), 7.66 (dd, J= 7.88, 4.68 Hz, 1H), 7.24 (m, 3H), 5.49 (s, 2H), 3.83 (s, 3H), 3.77(s, 3H); 13C-NMR (100 MHz, DMSO-d6): d 188.81, 166.12, 154.66, 153.55, 148.49, 146.69, 136.89, 133.04, 126.43, 124.89, 122.96, 1 15.79, 1 10.68, 67.44, 55.56, 52.34. MS (ESI) m/z found 324.08 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 98% pure.

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. 116986-09-5, Methyl 3-(bromomethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; THE CHILDREN’S HOSPITAL OF PHILADELPHIA; SAFO, Martin, K.; ZHANG, Yan; PARAGE, Piyusha, Pradeep; XU, Guoyan; GHATGE, Mohini; VENITZ, Jurgen; ABDULMALIK, Osheiza; (78 pag.)WO2019/182938; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 116986-09-5, 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. 116986-09-5, name is Methyl 3-(bromomethyl)picolinate. A new synthetic method of this compound is introduced below.

Step 1 : Preparation of methyl 3-[(2,3,5-trichloro-4-pyridyl)methylsulfanylmethyl]pyridine-2- carboxylate To a solution of S-[(2,3,5-trichloro-4-pyridyl)methyl] ethanethioate (17.7 g, 65.4 mmol) in methanol (200 ml) was added potassium carbonate (10.9 g, 78.9 mmol) and the mixture stirred for 5 min at room temperature. Methyl-3-(bromomethyl)pyridine-2-carboxylate (16.6 g, 72.2 mmol) was then added and the reaction mixture was stirred at room temperature for 1 h. Water was added and the organic phase separated. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with brine and dried over sodium sulfate. The residue after filtration and evaporation of the solvent was chromatographed on silica gel eluted with hexane:ethyl acetate (1 :1 ) to give 21.7 g (88%) of the desired product. 1H NMR (CDCIs): 8.62 (d, 1 H); 8.25 (s, 1 H); 7.87 (d, 1 H); 7.41 (dd, 1 H); 4.27 (s, 2H), 3.98 (s, 5H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,116986-09-5, its application will become more common.

Reference:
Patent; BASF SE; BESONG, Gilbert; WITSCHEL, Matthias; REINGRUBER, Ruediger; KRAUS, Helmut; SEITZ, Thomas; PARRA RAPADO, Liliana; NEWTON, Trevor William; KRAeMER, Gerd; EVANS, Richard Roger; RACK, Michael; WO2014/187705; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 116986-09-5, Adding some certain compound to certain chemical reactions, such as: 116986-09-5, name is Methyl 3-(bromomethyl)picolinate,molecular formula is C8H8BrNO2, 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 116986-09-5.

To a solution of S-[(6-chloro-4-methyl-3-pyridyl) methyl] ethanethioate (1.67 g, 7.8 mmol) in 50 mL methanol was added K2CO3 (2.14 g, 15.5 mmol). The mixture was stirred for 30 min at room temperature. Then methyl-(3-bromomethyl)pyridine-2-carboxylate (1 .78 g, 7.8 mmol) was added and it was stirred for 2.5 hours at room temperature. The mixture was concentrated to give the crude product (2.87 g, crude, MS+1 =322).

According to the analysis of related databases, 116986-09-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; WITSCHEL, Matthias; KRAUS, Helmut; HUTZLER, Johannes; NEWTON, Trevor William; REINGRUBER, Ruediger; FRASSETTO, Timo; PARRA RAPADO, Liliana; BESONG, Gilbert; RACK, Michael; KLOET, Andree van der; SEITZ, Thomas; LERCHL, Jens; KREUZ, Klaus; PASTERNAK, Maciej; EVANS, Richard Roger; WO2013/178585; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 116986-09-5, Adding some certain compound to certain chemical reactions, such as: 116986-09-5, name is Methyl 3-(bromomethyl)picolinate,molecular formula is C8H8BrNO2, 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 116986-09-5.

To a solution of S-[(6-chloro-4-methyl-3-pyridyl) methyl] ethanethioate (1.67 g, 7.8 mmol) in 50 mL methanol was added K2CO3 (2.14 g, 15.5 mmol). The mixture was stirred for 30 min at room temperature. Then methyl-(3-bromomethyl)pyridine-2-carboxylate (1 .78 g, 7.8 mmol) was added and it was stirred for 2.5 hours at room temperature. The mixture was concentrated to give the crude product (2.87 g, crude, MS+1 =322).

According to the analysis of related databases, 116986-09-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; WITSCHEL, Matthias; KRAUS, Helmut; HUTZLER, Johannes; NEWTON, Trevor William; REINGRUBER, Ruediger; FRASSETTO, Timo; PARRA RAPADO, Liliana; BESONG, Gilbert; RACK, Michael; KLOET, Andree van der; SEITZ, Thomas; LERCHL, Jens; KREUZ, Klaus; PASTERNAK, Maciej; EVANS, Richard Roger; WO2013/178585; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 116986-09-5, Adding some certain compound to certain chemical reactions, such as: 116986-09-5, name is Methyl 3-(bromomethyl)picolinate,molecular formula is C8H8BrNO2, 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 116986-09-5.

A mixture of 2,6-dihydroxybenzaldehyde (leq) and methyl 3-(bromomethyl)picolinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) ( 1 2eq) was added to this mixture and the reaction was stirred at room temperature for 4 hours. The solvent was then evaporated and the reaction mixture extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and the solvent evaporated. The crude product was purified using SiO2 column chromatography and eluted with the solvent system EtOAc: hexanes = 6: 1 to obtain pure product as pale yellow powder with a yield of 54%. IR (Diamond, cm-1): 3092, 2923, 2851, 1774, 1712, 1632, 1599, 1566, 1515, 1478, 1366, 1276, 1231 , 1 180, 1 136, 1072; 1H-NMR (400 MHz, DMSO-d6): d 1 1.72 (s, 1H), 10.32 (s, 1 H), 8.65 (dd, .7= 4.64, 1.52 Hz, 1H), 8.22 (m, 1 H), 7.66 (dd, J= 7.88, 4.64 Hz, 1 H), 7.54 (t, J= 8.4 Hz, 1H), 6.66 (d, T = 8 Hz, 1H), 6.57 (d, J = 8.4 Hz, 1H), 5.51 (s, 2H), 3.84 (s, 3H), 13C-NMR (100 MHz, DMSO-d6): d 193.59, 166.09, 162.46, 160.68, 148.53, 146.54, 138.72, 136.83, 132.78, 126.44, 1 10.74, 109.79, 103.26, 67.04, 52.35. MS (ESI) m/z found 310.08 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 100% pure.

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. 116986-09-5, Methyl 3-(bromomethyl)picolinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VIRGINIA COMMONWEALTH UNIVERSITY; THE CHILDREN’S HOSPITAL OF PHILADELPHIA; SAFO, Martin, K.; ZHANG, Yan; PARAGE, Piyusha, Pradeep; XU, Guoyan; GHATGE, Mohini; VENITZ, Jurgen; ABDULMALIK, Osheiza; (78 pag.)WO2019/182938; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 116986-09-5, 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. 116986-09-5, name is Methyl 3-(bromomethyl)picolinate, molecular formula is C8H8BrNO2, The 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 methyl 3-(bromomethyl)picolinate (6.0 g, 26.0 mmol) in CH3CN (200 mL) was added TBAF (10.2 g, 39.0 mmol) and TMSCN (5.2 g, 52.0 mmol) at 0 C. The mixture was stirred at 30 C for 16 h under N2. The solution was then diluted with DCM and washed with sat. NaC1. The organic layer was dried over Na2SO4 and concentrated in vacuum to give the crude product. This crude product was purified by column chromatography (PE:EA=5: 1–2: 1) to afford the desired product (2.3 g, 50.3%). ?H NMR (400MHz, CDC13) (ppm): 8.76 (dd, J=1.5, 4.6 Hz, 1H), 8.04 (td, J=0.8, 8.0 Hz, 1H), 7.58 (dd, J=4.6, 8.0 Hz, 1H), 4.31 (s, 2H), 4.04 (s, 3H). LCMS (mlz): 177.0 [M+H]+

According to the analysis of related databases, 116986-09-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; MUNCHHOF, Michael, John; SHAPIRO, Gideon; (393 pag.)WO2015/200677; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem