4-(1-furan-3-ylmethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylic acid tert-butyl ester → 1-furan-3-ylmethyl-3-piperidinyl-1H-pyrrolo[2,3-b]pyridine

HRID 1437171Notes

Reaction equation

HRID 1437171 reaction equation
C(OC(N1CCC([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:23][C:24]3[CH:28]=[CH:27][O:26][CH:25]=3)[CH:15]=2)CC1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[O:26]1[CH:27]=[CH:28][C:24]([CH2:23][N:16]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:22]3[C:14]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:17]3)=[CH:15]2)=[CH:25]1

Participants

4

Reactant 1

HCID 688949704-(1-furan-3-ylmethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 688947451-furan-3-ylmethyl-3-piperidinyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Over a solution of 1.4 g (3.7 mmol) of 4-(1-furan-3-ylmethyl-1H-pyrrolo[2,3-b]pyridin-3-yl) piperidine-1-carboxylic acid tert-butyl ester in 10 ml of dichloromethane, 2.85 ml of trifluoroacetic acid were carefully added. The crude mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the crude residue was dissolved in 10 ml of ethyl acetate and washed with saturated aqueous solution of sodium carbonate and brine. After drying over sodium sulphate, filtering and removing the solvent under reduced pressure, 0.62 g (60% of yield) of the expected product were obtained.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe crude residue was dissolved in 10 ml of ethyl acetate
  3. washwashed with saturated aqueous solution of sodium carbonate and brine
  4. dry with materialAfter drying over sodium sulphate
  5. filtrationfiltering
  6. customremoving the solvent

Sources & evidence

ORD record
ord-e32612334fe646fb9a9b1484dcd34702
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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