Trifluoroacetic acid → 3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)aniline

HRID 2240220Notes

Reaction equation

HRID 2240220 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16](COCC[Si](C)(C)C)[CH:17]=[CH:18][C:11]=12)[NH2:5].FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[CH:18][C:11]=12)[NH2:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593049903-Fluoro-4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]aniline

Product 1

HCID 593050333-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)aniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

477 mg (1.00 mmol) of 3-fluoro-4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]aniline are dissolved in 4 ml of dichloromethane. 4.0 ml of trifluoroacetic acid are added, and the mixture is stirred at RT for 2 hours. The solution is concentrated to dryness. The residue is taken up in 15 ml of THF, and 15 ml of an aqueous 1 M lithium hydroxide solution are added. The solution is stirred at RT for 20 hours and then concentrated, and water is added. The mixture is extracted with ethyl acetate. The extract is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC.

Workup

  1. concentrationThe solution is concentrated to dryness
  2. addition15 ml of an aqueous 1 M lithium hydroxide solution are added
  3. stirringThe solution is stirred at RT for 20 hours
  4. concentrationconcentrated
  5. additionwater is added
  6. extractionThe mixture is extracted with ethyl acetate
  7. dry with materialThe extract is dried over sodium sulfate
  8. customthe solvent is removed under reduced pressure
  9. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-f05717f6828649bbb02c420a02c1bc50
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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