Sodium Iodide → 3-Iodo-7-({4-methyl-2-[4-(trifluoromethyl)phenyl](1,3-thiazol-5-yl)}methoxy)chromen-4-one

HRID 1694645Notes

Reaction equation

HRID 1694645 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[C:7]([I:12])=[CH:8][O:9]2)=[CH:4][CH:3]=1.Cl[CH2:15][C:16]1[S:20][C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)=[N:18][C:17]=1[CH3:31].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[I:12][C:7]1[C:6](=[O:13])[C:5]2[C:10](=[CH:11][C:2]([O:1][CH2:15][C:16]3[S:20][C:19]([C:21]4[CH:22]=[CH:23][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:25][CH:26]=4)=[N:18][C:17]=3[CH3:31])=[CH:3][CH:4]=2)[O:9][CH:8]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazoleHCID 596606427-Hydroxy-3-iodo-4H-chromen-4-one

Product 1

HCID 596606493-Iodo-7-({4-methyl-2-[4-(trifluoromethyl)phenyl](1,3-thiazol-5-yl)}methoxy)chromen-4-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-hydroxy-3-iodochromen-4-one (864 mg, 3.0 mmol), 5-(chloromethyl)-4-methyl-2-(4-(trifluoromethyl)phenyl)thiazole) (875 mg, 3.0 mmol), sodium iodide (450 mg, 3.0 mmol), and potassium carbonate (552 mg, 4.0 mmol) was dissolved in N,N-dimethylformamide (10 ml) at room temperature under nitrogen. The mixture was heated at 600 for 1 hour, cooled to room temperature, and water (30 ml) added to the mixture. The aqueous mixture was extracted with methylene chloride (3×30 ml), and the combined organic layer washed with brine (30 ml), dried over sodium sulfate, and solvent removed from the filtrate under reduced pressure. Crystallization of the crude product from ethyl acetate (4 ml) gave 3-iodo-7-({4-methyl-2-[4-(trifluoromethyl)phenyl](1,3-thiazol-5-yl)}methoxy)chromen-4-one, a compound of formula (6).

Workup

  1. temperatureThe mixture was heated at 600 for 1 hour
  2. extractionThe aqueous mixture was extracted with methylene chloride (3×30 ml)
  3. washthe combined organic layer washed with brine (30 ml)
  4. dry with materialdried over sodium sulfate, and solvent
  5. customremoved from the filtrate under reduced pressure
  6. customCrystallization of the crude product from ethyl acetate (4 ml)

Sources & evidence

ORD record
ord-244a5ded49f945ceaedc92a1bc2305fc
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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