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Sodium hydride → 3-ethyl-N-methoxy-N-methyl-2-{[2-(trimethylsilyl)ethoxy]methyl}-2H-indazole-6-carboxamide

HRID 2240167
Notes
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Reaction equation

HRID 2240167 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([N:16]([O:18][CH3:19])[CH3:17])=[O:15])=[CH:11][CH:12]=2)[NH:7][N:6]=1)[CH3:4].[CH3:20][Si:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][O:24][CH2:25]Cl>O1CCCC1>[CH2:3]([C:5]1[N:6]([CH2:25][O:24][CH2:23][CH2:22][Si:21]([CH3:28])([CH3:27])[CH3:20])[N:7]=[C:8]2[C:13]=1[CH:12]=[CH:11][C:10]([C:14]([N:16]([O:18][CH3:19])[CH3:17])=[O:15])=[CH:9]2)[CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178438012HCID 178438012, compound

Product 1

HCID 598108303-ethyl-N-methoxy-N-methyl-2-{[2-(trimethylsilyl)ethoxy]methyl}-2H-indazole-6-carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent
2×

Conditions

Temperature
0 °C

Procedure

NaH (1.3 g, 60% dispersion in mineral oil, 0.033 mol) and tetrahydrofuran (223 mL) were mixed in a 1-necked flask and cooled to 0° C. To this was added dropwise a mixture of 3-ethyl-N-methoxy-N-methyl-1H-indazole-6-carboxamide (2.6 g, 0.011 mol) in tetrahydrofuran (60 mL), and the mixture was stirred at 0° C. for 1 hour. [β-(Trimethylsilyl)ethoxy]methyl chloride (2.4 mL, 0.013 mol) was then added and the reaction mixture was allowed to warm to room temperature. The resulting mixture was partitioned between water (50 mL) and ethyl acetate (50 mL). The layers were separated and the organics were washed with brine (25 mL), dried (sodium sulfate) and concentrated in vacuo to afford 4.0 g (quantitative yield) of 3-ethyl-N-methoxy-N-methyl-2-{[2-(trimethylsilyl)ethoxy]methyl}-2H-indazole-6-carboxamide, which was used without further purification.

Workup

  1. additionTo this was added dropwise
  2. temperatureto warm to room temperature
  3. customThe resulting mixture was partitioned between water (50 mL) and ethyl acetate (50 mL)
  4. customThe layers were separated
  5. washthe organics were washed with brine (25 mL)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05d18248db4140449c328892e4a6228f
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07723348B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes