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

HRID 2113710Notes

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]

Participants

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

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

Sources & evidence

ORD record: ord-4e5f698454894325b8b9cb3260f16bf6
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432266B2

Reaction notes

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