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Chemical Structure| 878198-71-1 Chemical Structure| 878198-71-1

Structure of 878198-71-1

Chemical Structure| 878198-71-1

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Product Details of [ 878198-71-1 ]

CAS No. :878198-71-1
Formula : C8H6ClFN2
M.W : 184.60
SMILES Code : FC1=CC=CC2=NC(CCl)=CN12
MDL No. :MFCD11656302

Safety of [ 878198-71-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 878198-71-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 878198-71-1 ]

[ 878198-71-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1597-32-6 ]
  • [ 534-07-6 ]
  • [ 878198-71-1 ]
YieldReaction ConditionsOperation in experiment
77% In ethyl acetate; at 65℃; for 15h; E) 2-(Chloromethyl)-5-fluoroimidazoH ,2-alpyridine: A solution of <strong>[1597-32-6]6-fluoro-2-pyridinamine</strong> (6.7 g, 60 mmol) in ethyl acetate (30 ml_) was treated with 1 ,3-dichloroacetone (15 g, 120 mmol) dissolved in ethyl acetate (15 ml_) and heated at 650C for 15 hours. The reaction was cooled to room temperature and the precipitate filtered, rinsed with acetone and ether, and dried to yield a tan solid. This intermediate was dissolved in water and treated with saturated aqueous sodium bicarbonate until the pH = 7. The precipitate was collected by filtration and dried to yield 2-(chloromethyl)-5- fluoroimidazo[1 ,2-a]pyridine (1.9 g, 77% yield) as a tan solid. 1H-NMR (CDCI3): δ 7.68 (s, 1H), 7.42 (d, 1H), 7.26-7.20 (m, 1H), 6.47 (dd, 1H), 4.76 (s, 2H).
77% 2-(Chloromethyl)-5-fluoroimidazori ,2-alpyridine: A solution of <strong>[1597-32-6]6-fluoro-2-pyridinamine</strong> (6.7 g, 60 mmol) in ethyl acetate (30 ml_) was treated with 1 ,3-dichloroacetone (15 g, 120 mmol) dissolved in ethyl acetate (15 ml_) and heated at 650C for 15 hours. The reaction was cooled to room temperature and the precipitate filtered, rinsed with acetone and ether, and dried to yield a tan solid. This intermediate was dissolved in water and treated with saturated aqueous sodium bicarbonate until the pH = 7. The precipitate was collected by filtration and dried to yield 2-(chloromethyl)-5-fluoroimidazo[1 ,2-a]pyridine (1.9 g, 77% yield) as a tan solid. 1H-NMR (CDCI3): δ 7.68 (s, 1 H), 7.42 (d, 1 H), 7.26-7.20 (m, 1 H), 6.47 (dd, 1H), 4.76 (s, 2H).
62% In 1,2-dichloro-ethane; at 40℃; for 48h; 2-(chloromethyl)-5-fluoroimidazoH ,2-alpyridine: 2,6-difluoropyridine (31.5 ml_, 0.348 mol) was diluted with 30% ammonium hydroxide(20OmL) in a steel bomb and heated to 110s C overnight. The bomb was cooled to room temperature over two hours then further cooled to 0Q C for two hours. The resulting solid was filtered and rinsed with water to obtain 26.39 g as a white solid. The filtrate was extracted with dichloromethane, dried over sodium sulfate and concentrated to afford an additional 9.3g (92% overall yield) of 6-fluoro-2- pyridinamine. A portion of the solid (5g, 0.044 mol) was dissolved in 1 ,2- dichloroethane (20 mL) and 1 ,3-dichloro-2-propanone (34.2 mL, 4.34 mol) was added in two portions. The reaction was stirred at 409 C over two days. The resulting solid was collected by filtration, dissolved in absolute ethanol (100 mL), and refluxed at 90Q C overnight. Solvent was evaporated and dichloromethane and saturated aqueous sodium bicarbonate was added to the residue. The aqueous layer was extracted two times with dichloromethane and once with a 3:1 chloroform: isopropanol mixture. Combined organics were dried over sodium sulfate and concentrated to a 3.61 g (62%) of 2-(chloromethyl)-5-fluoroimidazo[1 ,2-a]pyridine as a black oil which solidified upon standing. 1H NMR (400 MHz, DMSO-D6) δ 5.02 (s,2H), 7.29 (d, 1 H), 7.74 (d, 1 H), 7.88 (m, 1 H), 8.41 (s, 1 H); MS m/z 185 (M+1). EPO <DP n="47"/>B) 1 -[(5-fluoroimidazo[1 ,2-a]pyridin-2-yl)methyl]-1 ,2,3 ,4,4a,5,6,1 Ob-octahydro-1 ,10- phenanthroline:
 

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