2,3-Dihydro-5(4fluorophenyl)-6-(pyridin-4-yl)pyrazine → 2-(4-Fluorophenyl)-3-(pyridin-4-yl)pyrazine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[N:12][CH2:11][CH2:10][N:9]=2)=[CH:4][CH:3]=1>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[N:12][CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
The product of example 1 a above (0.1 g, 0.4 mmol) was treated with a solution of ferric chloride (0.13 g, 0.8 mmol) in ethanol (1 mL) and stirred at 50° C. for 12 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic phase dried over anhydrous Na2SO4, filtered, and evaporated to give the crude product which was chromatographed on silica gel eluted with 1-3% methanol in methylene chloride. Recrystallization from methylene chloride hexane gave the title compound as an white crystalline solid. ES (+) MS m/e=252 (MH+)
Workup
- customThe solvent was removed in vacuo
- customthe residue partitioned between ethyl acetate and water
- dry with materialThe organic phase dried over anhydrous Na2SO4
- filtrationfiltered
- customevaporated
- customto give the crude product which
- customwas chromatographed on silica gel
- washeluted with 1-3% methanol in methylene chloride
- customRecrystallization from methylene chloride hexane
Sources & evidence
- ORD record
- ord-2f6e6419f3b44832bd71304f809db662
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06861417B2
Reaction notes
Loading…