Potassium Iodide → HCID 19603780, compound

HRID 1604681Notes

Reaction equation

HRID 1604681 reaction equation
[H-].[Na+].[C:3]([C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)([CH3:6])([CH3:5])[CH3:4].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[CH:30]=2)[CH:25]=[CH:24]1.[I-].[K+]>CN(C)C=O>[C:3]([C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([CH2:21][N:23]4[C:31]5[C:26](=[CH:27][CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[CH:30]=5)[CH:25]=[CH:24]4)=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 639844Methyl indole-6-carboxylateHCID 19603727HCID 19603727, compound

Product 1

HCID 19603780HCID 19603780, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (84 mg, 60% in mineral oil) was added to a mixture of 4-tert-butyl-2-[5-(chloromethyl)benzofuran-2-yl]thiazole (0.40 g), methyl indole-6-carboxylate (0.28 g) and potassium iodide (0.22 g) in N,N-dimethylformamide (3 ml) and the mixture was stirred at room temperature. After being stirred at room temperature for 5 hours, the mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing the objective compounds were combined and concentrated under reduced pressure to give methyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}indole-6-carboxylate (0.40 g).

Workup

  1. stirringAfter being stirred at room temperature for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. washeluted with a mixture of toluene and ethyl acetate
  7. additionThe fractions containing the objective compounds
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-effd778b983f4a97bd7d9c869259827e
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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