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

HRID 2370377Notes

Reaction equation

HRID 2370377 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-fbb005cf5f314e81bebcfcccd5a172b3
Source dataset
uspto-grants-2014_04
Patent number
US08710085B2

Reaction notes

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