Sodium hydride → HCID 68698101, compound

HRID 887763Notes

Reaction equation

HRID 887763 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]([N:21]1[C:25]2[CH:26]=[CH:27][C:28]3[CH2:29][CH2:30][C:31](=O)[C:32]=3[C:24]=2[N:23]=[C:22]1[CH3:34])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1.O>[CH2:14]([N:21]1[C:25]2[CH:26]=[CH:27][C:28]3[CH2:29][CH2:30][C:31](=[CH:5][C:3]#[N:4])[C:32]=3[C:24]=2[N:23]=[C:22]1[CH3:34])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 59145911HCID 59145911, compound

Product 1

HCID 68698101HCID 68698101, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 60% sodium hydride (32 mg, 0.80 mmol) in tetrahydrofuran (5 mL) was added diethyl cyanomethylphosphonate (142 μL, 0.88 mmol), and the mixture was stirred at room temperature for 30 min. A solution of 3-benzyl-2-methyl-6,7-dihydroindeno[4,5-d]imidazol-8(3H)-one (73.4 mg, 0.27 mmol) in tetrahydrofuran (2 mL) was added thereto, and the mixture was stirred at room temperature for 30 min. The reaction solution was diluted with water, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20) to give the title compound (53.3 mg, yield 67%).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. extractionextracted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20)

Sources & evidence

ORD record
ord-84de4186938c4385be3759739a2522ef
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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