Trimethylsilyl cyanide → HCID 22387933, compound

HRID 1072806Notes

Reaction equation

HRID 1072806 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-b19709d5941f4ac5984e7a4694432b48
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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