Imidazole → HCID 59370713, compound

HRID 1873967Notes

Reaction equation

HRID 1873967 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:10])[CH:8]=2)[CH:3]=[N:2]1.CN(C=O)C.N1C=CN=C1.[CH3:21][C:22]([Si:25](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:24])[CH3:23]>C(OCC)(=O)C.O>[Si:25]([O:10][C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[N:2][NH:1]2)=[CH:5][CH:6]=1)([C:22]([CH3:24])([CH3:23])[CH3:21])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 1354839876-hydroxy-1H-indazole

Product 1

HCID 59370713HCID 59370713, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Indazol-6-ol (4.029 g) which can be prepared according to the method described in Reference example 35, etc. was dissolved dehydrated DMF (60 mL; manufactured by Kanto Chemical Co., Inc.), and added with imidazole (4.49 g; manufactured by Tokyo Chemical Industry, Co., Ltd.) and TBDPSCl (17.1 mL; manufactured by Tokyo Chemical Industry, Co., Ltd.). The mixture was stirred overnight at room temperature. The reaction solution was added to water and extraction was carried out three times with ethyl acetate. The organic layer was washed three times with water and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=92:8→71:29) to obtain the title compound (9.214 g).

Workup

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

Sources & evidence

ORD record
ord-2f1cebb63a504e058f3f088123477351
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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