Ethyl Acetate → HCID 68692311, compound

HRID 643351Notes

Reaction equation

HRID 643351 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH3:11].[H-].[Na+].[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17]OCCl.[C:23](OCC)(=[O:25])C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:23][O:25][CH:16]([Si:15]([CH3:14])([CH3:21])[CH3:22])[CH3:17])[N:6]=[C:5]2[CH3:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178434225HCID 178434225, compound

Product 1

HCID 68692311HCID 68692311, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromo-3-methyl-1H-indazole 104 (0.4 g, 1.89 mmol) in anhydrous DMF (4 mL) at 0° C. was added sodium hydride (0.068 g, 2.85 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (0.377 g, 2.26 mmol). The reaction mixture was stirred at 0° C. fro 1 hour. Ethyl acetate (100 mL) was added. The organic layer was washed with saturated ammonium chloride solution, water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to yield the desired 5-bromo-3-methyl-1-(trimethylsilyl)ethoxymethyl-1H-indazole 116 (0.369 g, 1.08 mmol).

Workup

  1. washThe organic layer was washed with saturated ammonium chloride solution, water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customThe organic solvent was evaporated under reduced pressure
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-2c813278ace640eda6a8709ccbb4e8cc
Source dataset
uspto-grants-2010_04
Patent number
US07700601B2

Reaction notes

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