Potassium Iodide → HCID 68414168, compound

HRID 915512Notes

Reaction equation

HRID 915512 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:9][C:10]1[N:11]=[CH:12][S:13][CH:14]=1.[CH3:15][NH:16][C:17]([C:19]1[C:23]2[CH:24]=[C:25]([O:33][CH:34]([CH3:36])[CH3:35])[C:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][C:22]=2[O:21][C:20]=1[C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)=[O:18].[I-].[K+]>C(#N)C>[CH3:15][NH:16][C:17]([C:19]1[C:23]2[CH:24]=[C:25]([O:33][CH:34]([CH3:36])[CH3:35])[C:26]([N:28]([S:29]([CH3:32])(=[O:30])=[O:31])[CH2:9][C:10]3[N:11]=[CH:12][S:13][CH:14]=3)=[CH:27][C:22]=2[O:21][C:20]=1[C:37]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=1)=[O:18]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27632894-(Chloromethyl)-1,3-thiazole hydrochlorideHCID 10409873HCID 10409873, compound

Product 1

HCID 68414168HCID 68414168, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (0.050 g, 0.357 mmol) followed by 4-(chloromethyl)thiazole hydrochloride (0.041 g, 0.238 mmol) were added to a solution of 2-(4-fluoro-phenyl)-5-isopropoxy-6-methanesulfonylamino-benzofuran-3-carboxylic acid methylamide (0.050 g, 0.119 mmol, which can be prepared according to one of the procedures described in Example 21 above), dissolved in acetonitrile (10 mL). The reaction was refluxed for 1 hour with no visible product formation observed by TLC, so potassium iodide (0.020 g, 0.120 mmol) was added to the reaction. The mixture was refluxed for an additional 2 hours, and then cooled to room temperature. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate and washed with water. The product was concentrated and purified by flash chromatography (silica gel, ethyl acetate/hexanes gradient) to provide 30 mg (48%) of the desired product as a white solid.

Workup

  1. customcan be prepared
  2. additionwas added to the reaction
  3. temperatureThe mixture was refluxed for an additional 2 hours
  4. concentrationThe reaction mixture was concentrated
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washwashed with water
  7. concentrationThe product was concentrated
  8. custompurified by flash chromatography (silica gel, ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-ab7eca47589f443aafb9a3d61aa0e44b
Source dataset
uspto-grants-2007_09
Patent number
US07265152B2

Reaction notes

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