Category: 116986-08-4

Application of 116986-08-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.116986-08-4, name is Methyl 2-(bromomethyl)nicotinate, molecular formula is C8H8BrNO2, molecular weight is 230.0586, as common compound, the synthetic route is as follows.

A mixture of 2,6-dihydroxybenzaldehyde (leq) and methyl 2-(bromomethyl)nicotinate (leq) was dissolved in anhydrous N,N-Dimethylformamide (DMF). Anhydrous potassium carbonate (K2CO3) (l.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 was 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 = 5:2 to obtain pure product as pale yellow powder with a yield of 58%. IR (Diamond, cm-1): 2956, 1713, 1618, 1637, 1571, 1459, 1435, 1396, 1370, 1287, 1238, 1 170, 1 141 ; 1H-NMR (400 MHz, DMSO-dfi): d 1 1.67 (s, 1H), 10.19 (s, 1 H), 8.75 (dd, .7= 4.8, 1.68 Hz, 1H), 8.25 (dd, J= 7.84, 1.68 Hz, 1 H), 7.55 (m, 2H), 6.66 (d, J = 8.2 Hz, 1 H), 6.53 (d, J = 8.4 Hz, 1H), 5.58 (s, 2H), 3.79(s, 3H); 13C-NMR (100 MHz, DMSO-d6): d 193.68, 166.15, 162.26, 161.44, 155.02, 151.73, 138.75, 138.31 , 126.02, 123.60, 1 10.66, 109.49, 103.51, 70.59, 52.50. MS (ESI) m/z found 288.09 (M+H)+, 310.07 (M+Na)+, Calculated 301.2940 [M]+. The purity of the compound was checked by HPLC and was found to be 100% pure.

The chemical industry reduces the impact on the environment during synthesis 116986-08-4, I believe this compound will play a more active role in future production and life.

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

Synthetic Route of 116986-08-4, 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. 116986-08-4, name is Methyl 2-(bromomethyl)nicotinate. A new synthetic method of this compound is introduced below.

To a solution of methyl 2-(bromomethyl)nicotinate (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 0C. The mixture was then stuffed at 30C for 16h under N2. The solution of the reaction was washed with water (30 mL) and extracted with EtOAc (15 mLx3). The organic layer was concentrated, and the residue was purified by column chromatography (PE:EA=5: 1–2: 1) to give the desired product (2.3 g, 50.3%). LCMS (mlz): 177.0 [M+H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,116986-08-4, Methyl 2-(bromomethyl)nicotinate, and friends who are interested can also refer to it.

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