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

HRID 558563Notes

Reaction equation

HRID 558563 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][CH:20]=[C:10]3[N:9]=2)=[CH:4][C:3]=1[CH3:21].C([O-])(=O)C.[Na+].[I:27]Cl>C(O)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[N:11]3[N:18]=[CH:19][C:20]([I:27])=[C:10]3[N:9]=2)=[CH:4][C:3]=1[CH3:21]

Participants

6

Reactant 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 670002385-(4-Chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670008925-(4-Chloro-3-methyl-phenyl)-3-iodo-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidineYield 93%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of 5-(4-chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine (4.57 g, 15.2 mmol) in acetic acid (25 mL) was added at room temperature sodium acetate (1.36 g, 16.6 mmol) and drop wise a solution of iodine monochloride (2.69 g, 16.6 mmol) in acetic acid (10 mL). The reaction mixture was stirred at room temperature for 19 h, diluted slowly with water (up to 100 mL), stirred at room temperature for 30 min, the precipitate was filtered off, washed with water and dried to give 5-(4-chloro-3-methyl-phenyl)-3-iodo-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine (5.96 g, 93%) as a yellow solid. MS (EI) 436.9 [(M)+]; mp 151° C.

Workup

  1. stirringstirred at room temperature for 30 min
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-39c15e1653d84ba592637013dce33d84
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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