5-Iodo-3-methylpyridin-2-amine → 2-Cyclopropyl-6-iodo-3,8-dimethylimidazo[1,2-a]pyridine

HRID 2202866Notes

Reaction equation

HRID 2202866 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([NH2:8])=[N:6][CH:7]=1.Br[CH:11]([CH3:17])[C:12]([CH:14]1[CH2:16][CH2:15]1)=O.[Cl-].[Cl-].[Ca+2]>CN(C=O)C>[CH:14]1([C:12]2[N:8]=[C:5]3[C:4]([CH3:9])=[CH:3][C:2]([I:1])=[CH:7][N:6]3[C:11]=2[CH3:17])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 9595865-Iodo-3-methylpyridin-2-amineHCID 5284359Calcium ChlorideHCID 450808052-Bromo-1-cyclopropylpropan-1-one

Product 1

HCID 1213862482-Cyclopropyl-6-iodo-3,8-dimethylimidazo[1,2-a]pyridineYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-iodo-3-methylpyridin-2-amine (100 mg), 2-bromo-1-cyclopropylpropan-1-one (113 mg) and DMF (1 ml) was stirred at 80° C. under a dry atmosphere (CaCl2 tube) overnight. The mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (69.3 mg) as a pale yellow oil.

Workup

  1. customThe mixture was quenched with saturated NaHCO3 solution
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-3e6693a7165f423fbdceff5e29b28df3
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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