2-Pyridinamine, 5-iodo- → HCID 86811355, compound

HRID 2202942Notes

Reaction equation

HRID 2202942 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:7][CH2:6]1)=O.[I:8][C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=1>CCO>[CH:5]1([C:3]2[N:15]=[C:12]3[CH:11]=[CH:10][C:9]([I:8])=[CH:14][N:13]3[CH:2]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 885792-Pyridinamine, 5-iodo-HCID 109208412-Bromo-1-cyclopropylethan-1-one

Product 1

HCID 86811355HCID 86811355, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-cyclopropylethanone (18.0 g), 5-iodopyridin-2-amine (5.2 g) and EtOH (100 ml) was heated at reflux for 16 h. The reaction mixture was then cooled to room temperature, and concentrated in vacuo. The resulting residue was diluted with DCM (200 ml), and washed with water (100 ml) and brine (100 ml). The DCM layer was dried over Na2SO4 and concentrated in vacuo. The crude product thus obtained was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (1.53 g) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. additionThe resulting residue was diluted with DCM (200 ml)
  5. washwashed with water (100 ml) and brine (100 ml)
  6. dry with materialThe DCM layer was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product thus obtained
  9. customwas purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-88be435157194b569bc380f0cb8352b5
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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