Iodine chloride → 3-Iodo-7-(trifluoromethyl)-5-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine

HRID 268981Notes

Reaction equation

HRID 268981 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[N:8]2[N:9]=[CH:10][CH:11]=[C:7]2[N:6]=[C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:4]=1.CC([O-])=O.[Na+].[I:29]Cl>C(O)(=O)C.O>[I:29][C:11]1[CH:10]=[N:9][N:8]2[C:3]([C:2]([F:1])([F:22])[F:23])=[CH:4][C:5]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=3)=[N:6][C:7]=12

Participants

6

Reactant 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 715397317-(Trifluoromethyl)-5-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 715397303-Iodo-7-(trifluoromethyl)-5-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidineYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (21.60 g, 65 mmol) in acetic acid (130 mL) containing anhydrous NaOAc (6.045 g, 74 mmol), was slowly added iodine monochloride (19.65 mL, 3.75M in HOAc). The reaction mixture was stirred at rt overnight. The suspension was diluted with water, the yellow crystalline filtrated, washed with water and dried in vacuum overnight to give 3-iodo-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (31.1 g, 100%) as yellow crystalline solid. MS (ISP) 458.2 [(M+H)+].

Workup

  1. washthe yellow crystalline filtrated, washed with water
  2. customdried in vacuum overnight

Sources & evidence

ORD record
ord-6c1c7781e25344cfbc93162b1dffb6e7
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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