Pyrazole → HCID 66521213, compound

HRID 2171240Notes

Reaction equation

HRID 2171240 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N: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.CC(N(C)C)=O>[N:1]1([C:18]2[CH:19]=[C:14]([NH2:13])[CH:15]=[N:20][CH:21]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

8

Reactant 4

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 8176813-Amino-5-bromopyridineHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 66521213HCID 66521213, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

Pyrazole (42 mg), cesium carbonate (340 mg), trans-N,N′-dimethylcyclohexan-1,2-diamine (74 mg), and copper iodide (50 mg) were added to a DMAc (2 ml) solution containing 5-bromopyridin-3-amine (90 mg) in a nitrogen atmosphere, followed by stirring in a sealed tube at 150° C. for 15 hours. The reaction solution was adjusted to room temperature and water was added, followed by extraction with ethyl acetate. The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 10:1). A brown solid of 5-(pyrazol-1-yl)pyridin-3-amine (56.7 mg) was thus obtained.

Workup

  1. customwas adjusted to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layers were washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 10:1)

Sources & evidence

ORD record
ord-5440768b8ca24408b051407adebe7834
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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