Sodium Iodide → HCID 57421270, compound

HRID 1097926Notes

Reaction equation

HRID 1097926 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:24])[C:11]([C:17]1[CH:22]=[CH:21][N:20]=[C:19](Cl)[CH:18]=1)([OH:16])[C:12]([F:15])([F:14])[F:13].[I-:25].[Na+].I>C(C(C)=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:24])[C:11]([C:17]1[CH:22]=[CH:21][N:20]=[C:19]([I:25])[CH:18]=1)([OH:16])[C:12]([F:15])([F:14])[F:13]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 574212633-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

Product 1

HCID 57421270HCID 57421270, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol (Example 132, 0.38 g) in ethyl-methyl ketone (5 mL) was treated with sodium iodide (600 mg) and HI-57% (0.132 mL) and heated for 2.5 h under reflux. The reaction mixture was then concentrated in vacuo, diluted with water, and pH adjusted to 7 with a saturated aqueous NaHCO3 solution. The mixture was extracted twice with ethyl acetate. The combined organic phases were washed with 0.5M sodium-thiosulfate and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (20 g silica gel, ethyl acetate/heptane 20:80) to give the title compound as white solid (375 mg). MS (m/e)=471.9 (MH+).

Workup

  1. temperatureheated for 2.5 h
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. additiondiluted with water
  5. extractionThe mixture was extracted twice with ethyl acetate
  6. washThe combined organic phases were washed with 0.5M sodium-thiosulfate and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (20 g silica gel, ethyl acetate/heptane 20:80)

Sources & evidence

ORD record
ord-98057eab661e4564b169456170f6ad3d
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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