Cesium carbonate → 5-iodo-1-pyridin-3-yl-1H-indazole

HRID 1661482

Reaction equation

HRID 1661482 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.Cl.Cl.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][NH2:26])[CH:20]=1>CN1CCCC1=O>[I:16][C:13]1[CH:12]=[C:9]2[C:8](=[CH:15][CH:14]=1)[N:25]([C:21]1[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=1)[N:26]=[CH:10]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 162170582-Fluoro-5-iodobenzaldehydeHCID 171324893-Hydrazinylpyridine dihydrochloride

Product 1

HCID 597865715-iodo-1-pyridin-3-yl-1H-indazoleYield 93.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Cesiumcarbonate (26.84 g, 82.38 mmol) is added to a suspension of 2-fluoro-5-iodobenzaldehyde (6.87 g, 27.46 mmol) and 3-pyridylhydrazine dihydrochloride (5 g, 27.46 mmol) in 136 mL N-methylpyrrolidon. The reaction mixture is stirred overnight at room temperature. After checking that the hydrazone has been formed (1H-NMR) the reaction mixture is heated for four hours at 160° C. The reaction mixture is allowed to cool down and the dark brown suspension is poured on 1000 mL ice water. After vigorously stirring at room temperature for 45 minutes, the precipitated product is sucked off via a glass microfibre filter, washed with water and dried at the evaporator at 45° C. 8.28 g (93.9%) of the title compound are obtained.

Workup

  1. customhas been formed (1H-NMR) the reaction mixture
  2. temperatureis heated for four hours at 160° C
  3. temperatureto cool down
  4. stirringAfter vigorously stirring at room temperature for 45 minutes
  5. filtrationfilter
  6. washwashed with water
  7. customdried at the evaporator at 45° C

Sources & evidence

ORD record
ord-5caddc39b2ab4bffb3eda6ad13631f43
Source dataset
uspto-grants-2011_10
Patent number
US08030340B2

Linked notes

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