Ethyl chloroformate → HCID 53727461, compound

HRID 651658Notes

Reaction equation

HRID 651658 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[C:9]([I:14])=[N:10][CH:11]=[CH:12][CH:13]=1>N1C=CC=CC=1>[CH2:5]([O:4][C:2](=[O:3])[NH:7][C:8]1[C:9]([I:14])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:6]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 181763372-Iodopyridin-3-amine

Product 1

HCID 53727461HCID 53727461, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl chloroformate (0.91 mL, 9.5 mmol) is added to a solution of 3-amino-2-iodo-pyridine (1.4 g, 6.36 mmol) in 15 mL of pyridine cooled at 0° C. The mixture is stirred at 0° C. for 2 hours and allowed to warm slowly to room temperature. At this time, excess pyridine is removed in vacuo. The residue is diluted with EtOAc and washed with water, 1N HCl and saturated NaHCO3. The organic layer is dried over MgSO4, filtered and concentrated in vacuo. The crude product is purified by column chromatography eluting with 30% EtOAc/hexanes to give the title compound (1.2 g, 4.11 mmol) as a beige solid.

Workup

  1. temperatureto warm slowly to room temperature
  2. customAt this time, excess pyridine is removed in vacuo
  3. additionThe residue is diluted with EtOAc
  4. washwashed with water, 1N HCl and saturated NaHCO3
  5. dry with materialThe organic layer is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by column chromatography
  9. washeluting with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-0ca9f03dcb824282a92b3c0d39f9325d
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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