2,6-Dichloro-4-iodopyridine → HCID 178511613, compound

HRID 2089036Notes

Reaction equation

HRID 2089036 reaction equation
[C@H:1]1([NH2:8])[CH2:6][CH2:5][C@H:4]([NH2:7])[CH2:3][CH2:2]1.[Cl:9][C:10]1[CH:15]=[C:14]([I:16])[CH:13]=[C:12](Cl)[N:11]=1>CCOC(C)=O>[Cl:9][C:10]1[N:11]=[C:12]([NH:7][C@H:4]2[CH2:5][CH2:6][C@H:1]([NH2:8])[CH2:2][CH2:3]2)[CH:13]=[C:14]([I:16])[CH:15]=1

Participants

4

Reactant 2

HCID 117373932,6-Dichloro-4-iodopyridineHCID 178511674HCID 178511674, compound

Product 1

HCID 178511613HCID 178511613, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of trans-cyclohexane-1,4-diamine (2.085 g, 18.26 mmol) and 2,6-dichloro-4-iodopyridine (1.000 g, 3.65 mmol) was heated in a capped vial at 120° C. After 5 hours, the reaction mixture was cooled. The solids were stirred in EtOAc for 30 minutes, and the suspension was filtered. The filtrate was diluted with EtOAc and washed with 20% brine and NaHCO3. The organic layer was dried and concentrated to give 1.20 g of the title compound. The crude product was used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationthe suspension was filtered
  3. additionThe filtrate was diluted with EtOAc
  4. washwashed with 20% brine and NaHCO3
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3b7f89dd3803406fbc368d74ee5cb5bf
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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