Trimethylsilyl iodide → HCID 56975984, compound

HRID 1358500Notes

Reaction equation

HRID 1358500 reaction equation
C([O:8][C@H:9]([C@H:11]([N:24]1[CH:28]=[C:27]([C:29]([NH2:31])=[O:30])[N:26]=[CH:25]1)[CH2:12][CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([Cl:23])[CH:21]=2)[CH:16]=[CH:15]1)[CH3:10])C1C=CC=CC=1.C[Si](I)(C)C>C(Cl)(Cl)Cl>[Cl:23][C:20]1[CH:21]=[C:22]2[C:17]([CH:16]=[CH:15][N:14]2[CH2:13][CH2:12][C@@H:11]([N:24]2[CH:28]=[C:27]([C:29]([NH2:31])=[O:30])[N:26]=[CH:25]2)[C@@H:9]([OH:8])[CH3:10])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 57248052HCID 57248052, compound

Product 1

HCID 56975984HCID 56975984, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To an ice cooled solution of 1-[(2S,3R)-2-benzyloxy-5-(6-chloroindol-1-yl)-3-pentyl]imidazole-4-carboxamide (47.9 mg, 0.110 mmol) in chloroform (5 ml) was added trimethylsilyl iodide (42.6 mg, 0.213 mmol). After 3 minutes, the ice bath was removed, and then stirred at room temperature for 3 hours. The reaction was quenched by addition of methanol. This mixture was extracted with ethyl acetate, and the extracts were washed with brine, dried (sodium sulfate) and evaporated in vacuo. The residue was purified by silica gel (1.5 g) chromatography eluting with chloroform/methanol (50:1 to 10:1) to give 1-[(2S,3R)-5-(6-chloroindol-1-yl)-2-hydroxy-3-pentyl]imidazole-4-carboxamide (20.1 mg, 52.7%).

Workup

  1. customthe ice bath was removed
  2. customThe reaction was quenched by addition of methanol
  3. extractionThis mixture was extracted with ethyl acetate
  4. washthe extracts were washed with brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel (1.5 g) chromatography
  8. washeluting with chloroform/methanol (50:1 to 10:1)

Sources & evidence

ORD record
ord-58a016a26078479a88a5175169dd0201
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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