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

HRID 1098896Notes

Reaction equation

HRID 1098896 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 r.t. After checking that the hydrazone has been formed (1H-NMR) the reaction mixture is heated for 4 h 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 r.t. for 45 min, 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 4 h at 160° C
  3. temperatureto cool down
  4. stirringAfter vigorously stirring at r.t. for 45 min
  5. filtrationfilter
  6. washwashed with water
  7. customdried at the evaporator at 45° C

Sources & evidence

ORD record
ord-19031bd0038e4074adb4246bc0b9ca97
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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