Triethylsilane → 1H-Pyrrolo(2,3-b)pyridine

HRID 392135Notes

Reaction equation

HRID 392135 reaction equation
ClCC([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=O.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O.CCOC(C)=O.C(=O)([O-])[O-].[Na+].[Na+]>[NH:7]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:13]2[CH:5]=[CH:6]1

Participants

6

Reactant 2

HCID 12052TriethylsilaneHCID 127782172-Chloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

Product 1

HCID 92221H-Pyrrolo(2,3-b)pyridine

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

A stirred solution of 2-chloro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone (12.5 g) in TFA at room temperature is treated with triethylsilane (72 mL, 7 eq.), stirred for 16 h, diluted with EtOAc and saturated sodium carbonate to pH 8. The phases are separated and the organic phase is dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, 10% EtOAc in ether as eluent) to give the title pyrrolo[2,3-b]pyridine compound, identified by NMR and mass spectral analyses.

Workup

  1. customThe phases are separated
  2. dry with materialthe organic phase is dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue is purified by flash chromatography (silica gel, 10% EtOAc in ether as eluent)

Sources & evidence

ORD record
ord-644db819d92143e694de752d883eecc0
Source dataset
uspto-grants-2004_10
Patent number
US06800640B2

Reaction notes

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