Imidazole → HCID 59370713, compound

HRID 1678708Notes

Reaction equation

HRID 1678708 reaction equation
[NH:1]1[CH:5]=[CH:4]N=C1.[CH3:6][C:7]([Si:10](Cl)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])[CH3:8].[OH2:24].C[N:26]([CH:28]=O)C>>[Si:10]([O:24][C:16]1[CH:4]=[C:5]2[C:13]([CH:28]=[N:26][NH:1]2)=[CH:12][CH:11]=1)([C:7]([CH3:9])([CH3:8])[CH3:6])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 6228DimethylformamideHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 59370713HCID 59370713, compound

Procedure

Indazol-6-ol (4.029 g) that can be produced by the method described in Reference Example 21 or the like, was dissolved in dehydrated DMF (60 mL; manufactured by Kanto Chemical Co., Inc.), and imidazole (4.49 g; manufactured by Tokyo Chemical Industry Co., Ltd.) and TBDPSCl (17.1 mL; manufactured by Tokyo Chemical Industry Co., Ltd.) were added to the solution. The mixture was stirred overnight at room temperature. The reaction solution was poured into water, and the mixture was extracted three times with ethyl acetate. The organic layer was washed three times with water, and was dried over anhydrous magnesium sulfate. Subsequently, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=92:8→71:29). Thus, the title compound (9.214 g) was obtained.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe organic layer was washed three times with water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customSubsequently, the solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=92:8→71:29)

Sources & evidence

ORD record
ord-e6f6a50a1d634bd693257802db073cbe
Source dataset
uspto-grants-2011_08
Patent number
US08008506B2

Reaction notes

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