Sodium hydride → (2E)-3-(5-bromo-2-methyl-2H-indazol-4-yl)acrylonitrile

HRID 1639799Notes

Reaction equation

[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[Br:14][C:15]1[CH:23]=[CH:22][C:21]2[C:17](=[CH:18][N:19]([CH3:24])[N:20]=2)[C:16]=1[CH:25]=O>O1CCCC1.[Cl-].[NH4+]>[Br:14][C:15]1[CH:23]=[CH:22][C:21]2[C:17](=[CH:18][N:19]([CH3:24])[N:20]=2)[C:16]=1/[CH:25]=[CH:3]/[C:1]#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of diethyl cyanomethylphosphonate (88.0 μL, 0.544 mmol) in tetrahydrofuran (2 mL) was added 60% sodium hydride (20.1 mg, 0.502 mmol) under ice-cooling, and the mixture was stirred at 0° C. for 15 min. To the mixture was added a solution of 5-bromo-2-methyl-2H-indazole-4-carbaldehyde (100 mg, 0.418 mmol) in tetrahydrofuran (2 mL) under ice-cooling, and the mixture was stirred for 15 min. The reaction solution was diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→80/20) to give the title compound (108 m yield 98%).

Workup

temperaturecooling
temperaturecooling
stirringthe mixture was stirred for 15 min
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→80/20)

Sources & evidence

ORD record: ord-e4877bf5a86e43c288b863f7e0152926
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110585B2

Reaction notes

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