Water → HCID 45280133, compound

HRID 1873958Notes

Reaction equation

HRID 1873958 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:24]([OH:26])[CH3:25])=[N:14][N:15]2[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:29]I.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:24]([O:26][CH3:29])[CH3:25])=[N:14][N:15]2[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59370708HCID 59370708, compound

Product 1

HCID 45280133HCID 45280133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(6-(Benzyloxy)-1-(tetrahydro-2H-pyran-2-yl)-indazol-3-yl) ethanol (10 mg) which can be prepared according to the method described in Reference example 24, etc. was dissolved in dehydrated DMF (0.12 mL; manufactured by Kanto Chemical Co., Inc.), added with sodium hydride-comprising 400 oil (2.0 mg; manufactured by Kanto Chemical Co., Inc.), followed by stirring at room temperature for 5 minutes. To the reaction solution, methyl iodide (4.87 μL; manufactured by Tokyo Chemical Industry, Co., Ltd.) was added and the mixture was stirred overnight at room temperature. Water was added to the reaction solution, which was then extracted twice with ethyl acetate. The organic layer was washed twice with water and once with brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography (“COLUMN-F”; n-hexane:ethyl acetate=5:1) to obtain the title compound (10.2 mg).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionwas then extracted twice with ethyl acetate
  3. washThe organic layer was washed twice with water and once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography (“COLUMN-F”; n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-2c8b79d06a7d4b12af4441a26b86cc5b
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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