Imidazole → HCID 66521378, compound

HRID 1620072Notes

Reaction equation

HRID 1620072 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].C[NH:13][C@@H:14]1[CH2:19][CH2:18]CC[C@H:15]1[NH:20][CH3:21].BrC1C=C(N)C=NC=1>[Cu](I)I.O.CN(C)C(=O)C>[N:1]1([C:18]2[CH:19]=[C:14]([NH2:13])[CH:15]=[N:20][CH:21]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 8176813-Amino-5-bromopyridineHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 66521378HCID 66521378, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

Imidazole (42 mg), cesium carbonate (340 mg), trans-N,N′-dimethylcyclohexane-1,2-diamine (74 mg), and copper iodide (50 mg) were added to a tube containing a N,N-dimethylacetamide (2 ml) solution containing 5-bromopyridin-3-amine (90 mg) in a nitrogen atmosphere and the tube was sealed, followed by stirring at 150° C. for 14.5 hours. The reaction solution was adjusted to room temperature, and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (chloroform:methanol=1:0 to 10:1), and a brown solid of 5-(1H-imidazol-1-yl)pyridin-3-amine (25.8 mg) was thus obtained.

Workup

  1. customthe tube was sealed
  2. customwas adjusted to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe resultant was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationSubsequently, the solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (chloroform:methanol=1:0 to 10:1)

Sources & evidence

ORD record
ord-040f12358315415ba3a077f1afd69057
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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