Triethylsilane → HCID 9814097, compound

HRID 1369168Notes

Reaction equation

HRID 1369168 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C@H:9]([NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[C:10]2=O)=[CH:6][CH:5]=1)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7](=[CH:6][CH:5]=1)[CH2:8][C@H:9]([NH:14][C:15](=[O:20])[C:16]([F:18])([F:17])[F:19])[CH2:10]2)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 9900550HCID 9900550, compound

Product 1

HCID 9814097HCID 9814097, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-[(2S)-6-Ethoxy-2,3-dihydro-1-oxo-1H-inden-2-yl]-2,2,2-trifluoroacetamide (V, EXAMPLE 4, 5.75 g, 20 mmol) is dissolved in 28.8 ml of trifluoroacetic acid and triethylsilane (9.6 ml, 60 mmol, 3 equiv.) is added. The reaction mixture is heated at reflux for 3 hr and then concentrated under reduced pressure. The product is partitioned between saturated sodium carbonate (30 ml) and ethyl acetate (60 ml). The organic layer is collected and concentrated to a solid. The solid is purified by flash chromatography eluting with ethyl acetate/hexane (3/7) to give the title compound; TLC Rf=0.64 (ethyl acetate/hexane; 30/70); NMR δ7.12, 6.75, 6.48, 4.76, 4.01, 3.32, 2.81 and 1.40; CMR δ58.7, 156.8, 141.2, 131.4, 125.4, 116.4, 113.8, 110.9, 63.6, 51.6, 39.9, 38.8 and 14.8; FMR (DMSO-d6) δ74.5. MS (CI, NH3) m/z (relative intensity) 291 (100), 273 (10), 243 (20), 160 (30), 132 (20). HRMS (FAB) calculated for C13H12F3NO2 [M+1]=272.0898, found=272.0896.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3 hr
  3. concentrationconcentrated under reduced pressure
  4. customThe product is partitioned between saturated sodium carbonate (30 ml) and ethyl acetate (60 ml)
  5. customThe organic layer is collected
  6. concentrationconcentrated to a solid
  7. customThe solid is purified by flash chromatography
  8. washeluting with ethyl acetate/hexane (3/7)

Sources & evidence

ORD record
ord-adaaa42042fc4f7d97139203c57be2a4
Source dataset
uspto-grants-2003_06
Patent number
US06576769B2

Reaction notes

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