Iodine chloride → HCID 67000825, compound

HRID 268987Notes

Reaction equation

HRID 268987 reaction equation
ClC1C=CC(C(=O)CC(=O)C(F)(F)F)=CC=1.NC1C=CNN=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[N:33]3[N:40]=[CH:41][CH:42]=[C:32]3[N:31]=2)=[CH:26][CH:25]=1.C([O-])(=O)C.[Na+].[I:48]Cl>C(O)(=O)C.O.CCOC(C)=O>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[C:34]([C:36]([F:37])([F:39])[F:38])[N:33]3[N:40]=[CH:41][C:42]([I:48])=[C:32]3[N:31]=2)=[CH:26][CH:25]=1

Participants

9

Reactant 5

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 8438385-(4-Chlorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidineHCID 27738321-(4-Chlorophenyl)-4,4,4-trifluorobutane-1,3-dioneHCID 178418806HCID 178418806, compound

Product 1

HCID 67000825HCID 67000825, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent3×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of commercially available 1-(4-chlorophenyl)-4,4,4-trifluoro-1,3-butanedione (8.65 g, 34.52 mmol) and commercially available 3-aminopyrazole (2.87 g, 34.52 mmol) in acetic acid (70 mL) was refluxed for 3 h (intermediate 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine). Cooled to 23° C., added sodium acetate (3.54 g, 43.2 mmol) and a solution of iodine monochloride (2.11 mL, 41.4 mmol) in acetic acid (12 mL) was added dropwise, whereupon the reaction mixture solidified 2 min after complete addition. Added acetic acid (50 mL) and the mixture was stirred at 23° C. for additional 1 h. Diluted slowly with water (up to 400 mL), stirred at 23° C. for 30 min, the precipitate was filtered off, washed with water and dried in air at 50° C. to give a yellow solid, which was dissolved in EtOAc, washed with sat. NaHCO3-sol. and sat. Na2SO3-sol. and brine, dried over Na2SO4. Removal of the solvent in vacuum gave 5-(4-chloro-phenyl)-3-iodo-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine as a yellow solid (14.30 g, 98%). MS (EI) 422.9 [(M)+] and 425.0 [(M+2)+]; mp 155° C.

Workup

  1. additionafter complete addition
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried in air at 50° C.
  5. customto give a yellow solid, which
  6. washwashed with sat. NaHCO3-sol
  7. dry with materialand brine, dried over Na2SO4
  8. customRemoval of the solvent in vacuum

Sources & evidence

ORD record
ord-e5b692bf939b49a5968824c7d8dd6f3e
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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