Trimethylsilyl cyanide → HCID 22387933, compound

HRID 1699828Notes

Reaction equation

HRID 1699828 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[N+:7]([O-])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]=1[CH3:20].C[Si]([C:30]#[N:31])(C)C.C(=O)([O-])O.[Na+]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][C:11]([C:30]#[N:31])=[CH:12][CH:13]=[C:8]2[N:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]=1[CH3:20]

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 86585542HCID 86585542, compound

Product 1

HCID 22387933HCID 22387933, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a suspension of ethyl 3-(2,4-dichlorobenzyl)-2-methylpyrrolo[3,2-b]pyridine-1-carboxylate N-oxide (414 mg) in anhydrous triethylamine (4 ml) was added trimethylsilylcyanide (704 mg) at room temperature in a nitrogen atmosphere, and the mixture was refluxed with heating overnight. The reaction mixture was cooled and a saturated aqueous sodium hydrogencarbonate solution was added. The mixture was extracted with ethyl acetate, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated, and the residue was subjected to flash silica gel chromatography (silica gel, 80 ml, eluted with hexane-ethyl acetate=5-1) and crystallized from isopropyl ether to give the objective compound (204 mg) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating overnight
  3. temperatureThe reaction mixture was cooled
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with water and saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated
  9. washthe residue was subjected to flash silica gel chromatography (silica gel, 80 ml, eluted with hexane-ethyl acetate=5-1)
  10. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-be3e2bb59aae4936a1a79bc05615bc0e
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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