Cyclohexylamine → 6-chloro-N-cyclohexyl-4-iodopyridin-2-amine

HRID 2088988Notes

Reaction equation

HRID 2088988 reaction equation
Cl[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH:10]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(OCC)(=O)C>[Cl:9][C:4]1[N:3]=[C:2]([NH:16][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[C:6]([I:8])[CH:5]=1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 117373932,6-Dichloro-4-iodopyridine

Product 1

HCID 866498506-chloro-N-cyclohexyl-4-iodopyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2,6-dichloro-4-iodopyridine (0.1 g, 0.36 mmol) was added excess (1 mL) cyclohexylamine. The reaction mixture was heated at 150° C. in a microwave for 20 minutes. The reaction mixture was cooled to room temperature and diluted with ethyl acetate, at which time a white solid precipitated from the solution. The solid was filtered off and the organics were washed with sodium bicarbonate, water, brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel by flash chromatography (gradient elution: 0% to 50% ethyl acetate/hexane) to afford the title compound as an oil. m/z 337.0 (DCI, M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customprecipitated from the solution
  3. filtrationThe solid was filtered off
  4. washthe organics were washed with sodium bicarbonate, water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel by flash chromatography (gradient elution: 0% to 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-712d667825704fd39c1a931a289bf1a8
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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