Water → 1-(4-chlorophenyl)-5-iodo-1H-indazole

HRID 13156

Reaction equation

HRID 13156 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.F[C:12]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:13]=1[CH:14]=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN1C(=O)CCC1>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:12]3[C:13](=[CH:16][C:17]([I:20])=[CH:18][CH:19]=3)[CH:14]=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 162170582-Fluoro-5-iodobenzaldehyde

Product 1

HCID 593397541-(4-chlorophenyl)-5-iodo-1H-indazole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-chlorophenylhydrazine hydrochloride (5.24 g, 29.27 mmol), 2-fluoro-5-iodobenzaldehyde (7.5 g, 30.00 mmol) and cesium carbonate (22.8 g, 69.98 mmol) was suspended in NMP (120 mL) and stirred at ambient temperature for 45 min. The temperature was raised to +160° C. and the reaction mixture was stirred for 1 h, the now black suspension was allowed to reach r.t. Water was added, the slurry was extracted with EtOAc (500 mL. The organic phase was washed with brine (2×). The brine fractions and waterphase was combined and backextracted once with EtOAc. This second EtOAc phase was washed with brine (2×) before combined with the previous EtOAc phase. The organic phases were dried over Na2SO4, filtered and evaporated. The black residue were dissolved in DCM/Heptane (=1/1) and filtered through a silica column, and the column was then further eluted with DCM/Heptane (=1/1) solvent mixture. The fractions containing product was evaporated, residue was dissolved in EtOAc and Heptane was added, evaporation and diluting with Heptane afforded a slurry, the solid material was collected by filtration and washed with Heptane. Yield 2.82 g (27%)

Workup

  1. temperatureThe temperature was raised to +160° C.
  2. stirringthe reaction mixture was stirred for 1 h
  3. customto reach r.t
  4. extractionthe slurry was extracted with EtOAc (500 mL
  5. washThe organic phase was washed with brine (2×)
  6. washThis second EtOAc phase was washed with brine (2×)
  7. dry with materialThe organic phases were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. dissolutionThe black residue were dissolved in DCM/Heptane (=1/1)
  11. filtrationfiltered through a silica column
  12. washthe column was then further eluted with DCM/Heptane (=1/1) solvent mixture
  13. additionThe fractions containing product
  14. customwas evaporated
  15. dissolutionresidue was dissolved in EtOAc
  16. additionHeptane was added
  17. customevaporation
  18. additiondiluting with Heptane
  19. customafforded a slurry
  20. filtrationthe solid material was collected by filtration
  21. washwashed with Heptane

Sources & evidence

ORD record
ord-7aa4926ed1224a53859f2146651fd925
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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