Cesium carbonate → 5-iodo-1-pyridin-2-yl-1H-indazole

HRID 1661479Notes

Reaction equation

HRID 1661479 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].F[C:8]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:9]=1[CH:10]=O.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][NH2:24]>CN1CCCC1=O>[I:16][C:13]1[CH:12]=[C:9]2[C:8](=[CH:15][CH:14]=1)[N:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=1)[N:24]=[CH:10]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 786452-HydrazinopyridineHCID 162170582-Fluoro-5-iodobenzaldehyde

Product 1

HCID 593397925-iodo-1-pyridin-2-yl-1H-indazole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Cesiumcarbonate (29.86 g, 91.6 mmol) is added to a suspension of 2-fluoro-5-iodobenzaldehyde (11.45 g, 45.8 mmol) and 2-pyridylhydrazine (5 g, 45.8 mmol) in 230 mL N-methylpyrrolidon. The reaction mixture is stirred two hours at room temperature. After checking that the hydrazone has been formed (1H-NMR) the reaction mixture is heated for three hours at 150° C. The reaction mixture is allowed to cool down and the dark brown suspension is poured into ice water. After vigorously stirring at room temperature for 15 minutes the mixture is extracted with ethyl acetate. The organic phase is washed with brine, dried over Na2SO4, the solvent is removed i.vac., and the product purified by chromatography on silica gel. Yield 4.8 g (33%).

Workup

  1. customhas been formed (1H-NMR) the reaction mixture
  2. temperatureis heated for three hours at 150° C
  3. temperatureto cool down
  4. stirringAfter vigorously stirring at room temperature for 15 minutes the mixture
  5. extractionis extracted with ethyl acetate
  6. washThe organic phase is washed with brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent is removed i.vac
  9. custom, and the product purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4accd67bcb83443ea8d5127187fc28ae
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Reaction notes

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