Trifluoroacetic acid → 2-piperazin-1-yl-1-[(4-pyridin-4-yl)phenyl]-1H-indole-3-carboxaldehyde

HRID 1678204Notes

Reaction equation

HRID 1678204 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=4)=[CH:27][CH:26]=3)[C:16]3[C:21]([C:22]=2[CH:23]=[O:24])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[N:11]1([C:14]2[N:15]([C:25]3[CH:26]=[CH:27][C:28]([C:31]4[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=4)=[CH:29][CH:30]=3)[C:16]3[C:21]([C:22]=2[CH:23]=[O:24])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86596815HCID 86596815, compound

Product 1

HCID 112690582-piperazin-1-yl-1-[(4-pyridin-4-yl)phenyl]-1H-indole-3-carboxaldehydeYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-Formyl-1-[(4-pyridin-4-yl)phenyl]-1H-indol-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (68 mg, 0.141 mmol) is dissolved in dichloromethane (1 mL), treated with trifluoroacetic acid (2 mL) and stirred for 2 hr at room temperature. The solvent is removed, the resulting oil is dissolved in water, made basic to pH around 7˜8 with 20% aq sodium hydroxide and extracted with dichloromethane. The combined organic layer is washed with brine and dried over sodium sulfate, filtered and concentrated. The residue is purified by chromatography eluting with dichloromethane-0 to 10% methanol to afford 2-piperazin-1-yl-1-[(4-pyridin-4-yl)phenyl]-1H-indole-3-carboxaldehyde (46 mg, 85%) as a light tan solid. ESI/MS 383 (M+1).

Workup

  1. customThe solvent is removed
  2. dissolutionthe resulting oil is dissolved in water
  3. extractionextracted with dichloromethane
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by chromatography
  9. washeluting with dichloromethane-0 to 10% methanol

Sources & evidence

ORD record
ord-fc870f5878c04931af10e6c8162cc48b
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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