Iodine chloride → 3-Iodo-8-methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

HRID 558593Notes

Reaction equation

HRID 558593 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([CH:18]=[CH:19][N:20]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:7]=1.C([O-])(=O)C.[Na+].[I:26]Cl>C(O)(=O)C>[I:26][C:18]1[N:4]2[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:15])[F:17])=[CH:10][CH:9]=3)[CH:7]=[C:2]([CH3:1])[C:3]2=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 670011108-Methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

Product 1

HCID 670001273-Iodo-8-methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridineYield 89.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 8-methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine (example C.20 step 2) (5.0 g, 18 mmol) in 50 mL of acetic acid was added sodium acetate (1.68 g, 20 mmol) and a solution of iodine monochloride (2M, 10.3 mL, 20.6 mmol)-slightly exothermic. The reaction mixture was stirred at 23° C. for 16 h, then partitioned between 300 mL of water and 300 mL of EtOAc. The organic layer was washed with sat. NaHCO3, water, aq. sodium sulfite, water, then dried over Na2SO4, filtered and concentrated to give the title compound as an off-white solid (6.47 g, 89%). MS (ISP) 403.3 [(M+H)+].

Workup

  1. custompartitioned between 300 mL of water and 300 mL of EtOAc
  2. washThe organic layer was washed with sat. NaHCO3, water, aq. sodium sulfite, water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1aba33b7583c4f328fa160a39803fbec
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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