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

HRID 558543Notes

Reaction equation

HRID 558543 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-2b742a7ccada41c982659946d8c0330c
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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