Category: 101990-73-2

Related Products of 101990-73-2, 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. 101990-73-2, name is 2-Chloro-4-(chloromethyl)pyridine. A new synthetic method of this compound is introduced below.

Preparation of ethyl 5~rr(2-chloropyridin-4-yl)methyll(formyl)aminol-l- methyl- 1 H-pyrazole-4-carboxylateA solution of crude ethyl 5-(formylamino)-l -methyl- 1 H-pyrazole-4-carboxylate (3.0Og, 15.21mmol) from step 1 in dichloromethane (30ml) was treated with diazabicyclo(5.4.0)undec-7-ene (3.41ml, 22.82mmol) and allowed to stir at room temperature for 30 minutes. 2-Chloro-4-chloromethylpyridine (4.93g, 30.43mmol) was added, and the reaction mixture was allowed to stir at room temperature for 16 h. The reaction mixture was then diluted with DCM and washed with concentrated NaHCO3 solution, followed by water, then brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was washed with ether, and the ether washings were concentrated and triturated with hexanes. The residue was again concentrated yielding 3.93g (80.1%) product as a thin oil.1R NMR (300 MHz, CD3CN) ? 8.30 (d, IH), 8.23 (s, IH), 7.85 (s, IH), 7.33 (s, IH), 7.22 (d, IH), 4.80 (bs, 2H), 4.17 (q, 2H), 3.67 (s, 3H), 1.23 (t, 3H); ES-MS m/z 323.1 [M+H]+, HPLC RT (min) 2.31.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,101990-73-2, 2-Chloro-4-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/133006; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 101990-73-2 ,Some common heterocyclic compound, 101990-73-2, molecular formula is C6H5Cl2N, 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.

Chlorotrimethylsilane (2.7 muL, 0.021 mmol) and 1,2-dibromoethane (3.2 muL, 0.043 mmol) were added to a suspension of zinc (84 mg, 1.28 mmol) in THF (1.5 mL) and the mixture was stirred at 65 C. for 20 min. The mixture was cooled to 0 C., treated dropwise with a solution of 2-chloro-4-(chloromethyl)pyridine (139 mg, 0.856 mmol) in THF (0.5 mL) and stirred for 20 min. A solution of 4-bromo-5-fluoro-2,3-dimethyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-7-carbonitrile [Example 181A] (170 mg, 0.428 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium(II) chloride (27.9 mg, 0.043 mmol) was added and the mixture was slowly warmed to room temperature and stirred for 1 h. The mixture was heated at 60 C. overnight, then was cooled to room temperature and filtered through a pad of CELITE. The filtrate was diluted with DCM, washed sequentially with saturated aqueous NaHCO3 and water, and dried and concentrated. The residue was subjected to column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-50%), to provide 4-((2-chloropyridin-4-yl)methyl)-5-fluoro-2,3-dimethyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-7-carbonitrile as a yellow glassy solid (168.5 mg, 75% yield). Mass spectrum m/z 444, 446 (M+H)+.

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. 101990-73-2, 2-Chloro-4-(chloromethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Liu, Qingjie; Watterson, Scott Hunter; Batt, Douglas G.; Ahmad, Saleem; Beaudoin Bertrand, Myra; Gong, Hua; Guo, Weiwei; Macor, John E.; Ngu, Khehyong; Tebben, Andrew J.; Tino, Joseph A.; (177 pag.)US2016/115126; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 101990-73-2, 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. 101990-73-2, name is 2-Chloro-4-(chloromethyl)pyridine, molecular formula is C6H5Cl2N, 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.

A mixture of 2-chloro-4-((5-methyl-3-(5- phenylfuran-2-yl)-lH-l,2,4-triazol-l-yl) methyl)pyridine and 2-chloro-4-((3- methyl-5-(5-phenylfuran-2-yl)-lH-l,2,4-triazol-l -yl)methyl)pyridine (100 mg, 0.3 mmol) was treated with 1-methylpiperazine (280 mg, 3 mmol) in DIEA (10 ml), and refluxed overnight. The mixture was cooled, concentrated, treated with H20 (30 mL) and extracted with EtOAc (3 x 30 mL). The combined organic layers were washed with H20 (1 x 10 mL) and brine (1 x 10 mL), dried over Na2S04, filtered, and concentrated to afford the crude product, which was purified by prep-HPLC (Mobile phase: A = 0.1% NH4OH/H20, B = MeCN; Gradient: B = 60%-95% in 18 min; Column: XBridge (C18, 5um, 30mm x 150mm) to give l-methyl-4-(4-((5- methyl-3-(5-phenylfuran-2-yl)-lH-l,2,4-triazol-l-yl)methyl)pyridin-2-yl)piperazine as a yellow solid (66 mg, 53%) and l-methyl-4-(4-((3-methyl-5-(5-phenylfuran-2- yl)-lH-l,2,4-triazol-l-yl)methyl)pyridin-2-yl)piperazine as a yellow solid (42 mg, 34%). For l-methyl-4-(4-((5-methyl-3-(5-phenylfuran-2-yl)-lH-l,2,4-triazol-l-yl)methyl) pyridin-2-yl)piperazine: MS (ES+) C24H26N60 requires: 414, found: 415 [M+H]+. *H NMR (500 MHz, CDC13) delta 8.14 (d, 7 = 5.1 Hz, 1H), 7.89 – 7.72 (m, 2H), 7.39(t, / = 7.8 Hz, 2H), 7.28 (td, / = 7.4, 1.3 Hz, 1H), 7.04 (d, / = 3.5 Hz, 1H), 6.76 (d, J = 3.5 Hz, 1H), 6.44 – 6.26 (m, 2H), 5.26 (s, 2H), 3.53 (t, J = 5.0 Hz, 4H), 2.48 (t, / = 5.1 Hz, 4H), 2.44 (s, 3H), 2.32 (s, 3H). [0250] For l-methyl-4-(4-((3-methyl-5-(5-phenylfuran-2-yl)-lH-l,2,4-triazol- l-yl)methyl) pyridin-2-yl)piperazine: MS (ES+) C24H26N6O requires: 414, found: 415 [M+H]+. *H NMR (500 MHz, CDC13) delta 8.12 (d, / = 5.1 Hz, 1H), 7.63 – 7.55 (m, 2H), 7.38 (t, 7 = 7.6 Hz, 2H), 7.30 (dd, / = 14.4, 6.9 Hz, 1H), 7.11 (d, 7 = 3.5 Hz, 1H), 6.77 (d, / = 3.6 Hz, 1H), 6.51 – 6.40 (m, 2H), 5.60 (s, 2H), 3.46 (t, / = 5.1 Hz, 4H), 2.45 (s, 3H), 2.43 (t, / = 5.1 Hz, 4H), 2.30 (s, 3H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 101990-73-2, 2-Chloro-4-(chloromethyl)pyridine.

Reference:
Patent; JONES, Philip; DIFRANCESCO, Maria, Emilia; PETROCCHI, Alessia; CARROLL, Christopher, L.; MARSZALEK, Joe; CZAKO, Barbara; JOHNSON, Ryan; THEROFF, Jay; WO2014/31936; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 101990-73-2, name is 2-Chloro-4-(chloromethyl)pyridine, molecular formula is C6H5Cl2N, 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. Recommanded Product: 2-Chloro-4-(chloromethyl)pyridine

To a solution of 6-methyl-3-(5-(4-(trifluoromethoxy)phenyl)-l,3,4-oxadiazol-2- yl)pyridin-2(lH)-one (177 mg, 0.52 mmol) in DMF (10 mL) was added Cs2C03(652 mg, 2.0 mmol), Nal (15 mg, 0.10 mmol) and 2-chloro-4- (chloromethyl)pyridine (172 mu, 1.40 mmol). The reaction mixture was heated at 65 C for 16 hours. The reaction mixture was allowed to cool to RT, brine was added, and the aqueous phase was extraced with EtOAc (3 X 10 mL). The combined organic phases were dried over Na2S04, filtered, and the solvent was evaporated. The residue was purified by Biotage (SNAP 25, 20% to 100% EtOAc in hexanes, followed by 2% to 30%MeOH in DCM) to provide 2-(2-((2-chloropyridin-4- yl)methoxy)-6-methylpyridin-3-yl)-5-(4-(trifluoromethoxy)phenyl)- 1,3,4- oxadiazole (132 mg, 28%), and l-((2-chloropyridin-4-yl)methyl)-6-methyl-3-(5-(4- (trifluoromethoxy)phenyl)-l,3,4-oxadiazol-2-yl)pyridin-2(lH)-one (183 mg, 39%). MS (ES+)2-(2-((2-chloropyridin-4-yl)methoxy)-6-methylpyridin-3-yl)-5-(4- (trifluoromethoxy)phenyl)-l,3,4-oxadiazole C2iHi4QF3N4C>3 requires: 462/464, found: 463/465 [M+H]+; l-((2-chloropyridin-4-yl)methyl)-6-methyl-3-(5-(4- (trifluoromethoxy)phenyl)-l ,3,4-oxadiazol-2-yl)pyridin-2(lH)-one MS (ES+) C2iH14ClF3N403requires: 462, found: 463 [M+H]+; *H NMR (600 MHz, MeOH- d4) (58.36 (d, / = 5.3Hz, 1H), 8.34 (d, / = 7.4 Hz, 1H), 8.19 (d, / = 7.7 Hz, 2H), 7.33 (d, J = 7.7 Hz, 2H),7.26 (s, 1H), 7.05 (d, J = 5.3 Hz,lH),6.35 (d, J = 7.4 Hz,lH),5.42 (s, 2H), 2.31 (s, 3H).

With the rapid development of chemical substances, we look forward to future research findings about 101990-73-2.

Reference:
Patent; JONES, Philip; DIFRANCESCO, Maria, Emilia; PETROCCHI, Alessia; MARSZALEK, Joe; LIU, Gang; KANG, Zhijun; CARROLL, Christopher, L.; MCAFOOS, Timothy; CZAKO, Barbara; WO2014/31928; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 101990-73-2, name is 2-Chloro-4-(chloromethyl)pyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 101990-73-2

To a solution of ethyl 5-methyl-lH-l ,2,4-triazole-3-carboxylate (50 mg, 0.28 mmol) and 2-chloro-4-(chloromethyl)pyridine (50 mg, 0.31 mmol) in DMF (2 mL), K2CO3 (116 mg, 0.84mmol) was added. The mixture was stirred at RT overnight, and was then diluted with H20 (20 mL), extracted with EtOAc (3 x 20 mL), 4: 1 CHCl3: PrOH (3 x 20 mL), dried with MgS04 and concentrated under reduced pressure. The crude product was purified on a Biotage pre-packed silica gel column (EtOAc:Hexane 12% to 100% EtOAc) to afford ethyl l-((2- chloropyridin-4-yl)methyl)-5-methyl-lH-l ,2,4-triazole-3-carboxylate (29 mg, 40%) as a white solid. MS(ES+) Ci2H13ClN402 requires: 280 found: 281 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 101990-73-2, 2-Chloro-4-(chloromethyl)pyridine.

Reference:
Patent; JONES, Philip; DIFRANCESCO, Maria, Emilia; PETROCCHI, Alessia; CARROLL, Christopher, L.; MARSZALEK, Joe; CZAKO, Barbara; JOHNSON, Ryan; THEROFF, Jay; WO2014/31936; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem