Dimethyl Sulfoxide → HCID 68688975, compound

HRID 2238652Notes

Reaction equation

HRID 2238652 reaction equation
F[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][N:3]=1.[C:9]1([C@@H:15]([NH2:17])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CS(C)=O>C(OCC)(=O)C>[I:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:17][C@H:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:16])[CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 758181-Phenethylamine, (-)-HCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 68688975HCID 68688975, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 1 g of 2-fluoro-4-iodopyridine (synthesized according to a method disclosed in J. Org. Chem. 1993, 58, 7832-7838), 1.73 mL of (1S)-1-phenylethylamine, and 20 mL of dimethylsulfoxide, was stirred overnight at 80° C. The reaction mixture was cooled back to room temperature, then diluted with ethyl acetate, and washed with water and saturated brine in the subsequent order. The obtained organic layer was dried over anhydrous magnesium sulfate, then the insolubles were filtered, the filtrate was concentrated under reduced pressure, and the thus obtained residue was purified by silica gel column chromatography, to obtain 744 mg of 4-iodo-N-[(1S)-1-phenylethyl]-2-pyridinamine [58-1] as a light brown solid.

Workup

  1. customsynthesized
  2. washwashed with water and saturated brine in the subsequent order
  3. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe insolubles were filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe thus obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e41cb20d5ef04f1cb90d4fe309a6c74b
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

Loading…