Diethylamine → N,N-Diethyl-4-iodopyridin-2-amine

HRID 444875Notes

Reaction equation

HRID 444875 reaction equation
F[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][N:3]=1.[CH2:9]([NH:11][CH2:12][CH3:13])[CH3:10].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[CH2:9]([N:11]([CH2:12][CH3:13])[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][N:3]=1)[CH3:10]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 57417095N,N-Diethyl-4-iodopyridin-2-amineYield 92.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-fluoro-4-iodopyridine (2 g, 8.97 mmol), diethyl amine (2.77 ml, 26.9 mmol, 3 eq) and K2CO3 (2.48 g, 17.94 mmol, 2 eq) in DMF (20 mL) is stirred for 18 h at 100° C., allowed to cool to rt, diluted with EtOAc/H2O and extracted with EtOAc. The organic phase is washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue purified by silica gel column chromatography (Hex/Et2O, 98:2) to afford 2.3 g of the title compound as a yellow oil: ESI-MS: 277.1 [M+H]+; TLC: Rf=0.52 (Hex/Et2O, 98:2).

Workup

  1. temperatureto cool to rt
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue purified by silica gel column chromatography (Hex/Et2O, 98:2)

Sources & evidence

ORD record
ord-05451b44a9c14e41a505fa820cde1a77
Source dataset
uspto-grants-2013_07
Patent number
US08476268B2

Reaction notes

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