Water → 5-isopropenyl-1H-pyrrolo[2,3-b]pyridine

HRID 1261035Notes

Reaction equation

HRID 1261035 reaction equation
C([Si](C(C)C)(C(C)C)[N:5]1[C:9]2=[N:10][CH:11]=[C:12]([C:14](O)([CH3:16])[CH3:15])[CH:13]=[C:8]2[CH:7]=[CH:6]1)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.O>C(#N)C>[C:14]([C:12]1[CH:13]=[C:8]2[CH:7]=[CH:6][NH:5][C:9]2=[N:10][CH:11]=1)([CH3:16])=[CH2:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 497589892-(1-(Triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)propan-2-ol

Product 1

HCID 580868105-isopropenyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-propan-2-ol (97, 0.500 g, 1.5 mmol) in acetonitrile (10.0 mL) were added triethylsilane (1.00 mL, 6.3 mmol) and trifluoroacetic acid (0.50 mL, 6.5 mmol) under an atmosphere of nitrogen. The reaction was refluxed for 3 hours, then cooled down to room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 50% ethyl acetate in hexane to give the compound (98, 0.200 g, 84%). MS (ESI) [M+H+]+=159.

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 50% ethyl acetate in hexane
  9. customto give the compound (98, 0.200 g, 84%)

Sources & evidence

ORD record
ord-c1687085fe724b65b60804a5db757d00
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

Loading…