Sodium hydride → HCID 90314683, compound

HRID 1505766Notes

Reaction equation

HRID 1505766 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[NH:7][N:6]=[CH:5]2.[H-].[Na+].[CH3:17][Si:18]([CH3:25])([CH3:24])[CH2:19][CH2:20][O:21][CH2:22]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[N:7]([CH2:22][O:21][CH2:20][CH2:19][Si:18]([CH3:25])([CH3:24])[CH3:17])[N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 24728927Methyl 5-bromo-1H-indazole-7-carboxylate

Product 1

HCID 90314683HCID 90314683, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon atmosphere, a solution of methyl 5-bromo-1H-indazole-7-carboxylate (as prepared according to WO2008/65508) (658 mg) in DMF (20 mL) was stirred under ice-cooling. 60% Sodium hydride (124 mg) was added slowly, and the mixture was stirred for 30 minutes at the same temperature. 2-(Trimethylsilyl)ethoxymethyl chloride (544 μL) was added dropwise slowly using a syringe, and the mixture was stirred at room temperature for 4 hours. The mixture was poured into ice water and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified on silica gel column chromatography to obtain the titled compound (696 mg) as slightly yellow oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed sequentially with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-5a360ff38f2244819b055865f800bb68
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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