Triethylsilane → HCID 22611650, compound

HRID 1737768Notes

Reaction equation

HRID 1737768 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[C:16]1[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH:21]=1)=[O:5].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)=[O:5]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 22611488HCID 22611488, compound

Product 1

HCID 22611650HCID 22611650, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 0.40 gm (1.04 mMol) 5-(2-chloro-4-fluorobenzoyl)amino-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 5.2 mL trifluoroacetic acid were added 0.208 mL (1.3 mMol) triethylsilane and the reaction mixture was stirred at ambient. After 2 hours, the reaction mixture was concentrated under reduced pressure. To the residue was added 2N sodium hydroxide and the aqueous was extracted with dichloromethane. The combined organic extracts were washed with 2N sodium hydroxide, dried over sodium sulfate and then concentrated under reduced pressure to give an orange foam. The foam was subjected to radial chromatography (2 mm silica), eluting with 100:10:1 dichloromethane:methanol:ammonium hydroxide. The residue was crystallized from ethyl acetate/hexanes to give 0.27 gm (67.3%) of the title compound as a burnt orange powder.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added 2N sodium hydroxide
  3. extractionthe aqueous was extracted with dichloromethane
  4. washThe combined organic extracts were washed with 2N sodium hydroxide
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give an orange foam
  8. washeluting with 100:10:1 dichloromethane
  9. customThe residue was crystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e670468d94a34c188fab4b9d1d6c108c
Source dataset
uspto-grants-1999_10
Patent number
US05962474

Reaction notes

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