Water → 4-[(3-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]-3-fluoroaniline

HRID 2240246Notes

Reaction equation

HRID 2240246 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)C(F)(F)F)=[CH:14][C:13]=2[F:25])[N:4](COCC[Si](C)(C)C)[CH:3]=1.FC(F)(F)C(O)=O.O.[OH-].[Li+]>ClCCl>[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[F:25])[NH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 59305018N-{4-[(3-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]-3-fluorophenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 593050064-[(3-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]-3-fluoroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

567 mg (1.13 mmol) of N-{4-[(3-chloro 1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]-3-fluorophenyl}-2,2,2-trifluoroacetamide are dissolved in 5 ml of dichloromethane. 5 ml (65 mmol) of trifluoroacetic acid are added, and the mixture is stirred at RT for 3 h. The mixture is then concentrated, EA is added and the mixture is washed with sat. sodium carbonate solution. The organic phase is dried over sodium sulfate and concentrated. The residue is taken up in 35 ml of THF, and 15 ml of water and 542 mg (22.7 mmol) of lithium hydroxide are added. The mixture is stirred at RT for 20 h. The mixture is then concentrated under reduced pressure, and the residue is diluted with water. The mixture is extracted with ethyl acetate and the extract is dried over sodium sulfate and concentrated. The residue is purified by chromatography on silica gel (mobile phase dichloromethane:methanol 25:1). This gives crystals.

Workup

  1. concentrationThe mixture is then concentrated
  2. additionEA is added
  3. washthe mixture is washed with sat. sodium carbonate solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated
  6. stirringThe mixture is stirred at RT for 20 h
  7. concentrationThe mixture is then concentrated under reduced pressure
  8. additionthe residue is diluted with water
  9. extractionThe mixture is extracted with ethyl acetate
  10. dry with materialthe extract is dried over sodium sulfate
  11. concentrationconcentrated
  12. customThe residue is purified by chromatography on silica gel (mobile phase dichloromethane:methanol 25:1)

Sources & evidence

ORD record
ord-009008545e0445beac138539282f6480
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

Loading…