Triphenylphosphine → HCID 86691882, compound

HRID 517742Notes

Reaction equation

HRID 517742 reaction equation
[C:1]([O:4][CH2:5][C:6](=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[Si]([N:42]=[N+:43]=[N-:44])(C)C>C1COCC1.CCOC(C)=O>[C:1]([O:4][CH2:5][C:6]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=2)[N:44]=[N:43][N:42]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 66654601HCID 66654601, compound2×

Product 1

HCID 86691882HCID 86691882, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-oxo-2-{[5-(trifluoromethyl)-2-pyridinyl]amino}ethyl acetate (Intermediate 56, 3.30 g, 12.6 mmol) in THF at 0° C. were added triphenylphosphine (8.24 g, 31.4 mmol) and diisopropyl azodicorboxylate (6.30 g, 31.2 mmol). The reaction mixture was stirred for 30 min and trimethylsilyl azide (3.60 g, 31.2 mmol) was added dropwise at room temperature. The reaction mixture was heated to reflux for 4 hr. The reaction mixture was diluted with EtOAc and washed with ice water, aq. NaHCO3 solution and saturated brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford the crude product. This was purified by column chromatography (60-120 mesh silica gel), eluting with 20% ethyl acetate/pet ether, to give the title compound (1.80 g) as a pale yellow liquid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hr
  3. washwashed with ice water, aq. NaHCO3 solution and saturated brine solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product
  7. customThis was purified by column chromatography (60-120 mesh silica gel)
  8. washeluting with 20% ethyl acetate/pet ether

Sources & evidence

ORD record
ord-9b95444fc8e041b1b8693c84d700606d
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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