Potassium Fluoride → HCID 76567996, compound

HRID 1728119Notes

Reaction equation

HRID 1728119 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[C:29]([O:30][CH2:31][CH2:32][OH:33])=[CH:28][CH:27]=[C:26]([C:34]#[C:35][Si](C)(C)C)[C:25]=3[F:40])[C:5]2=[CH:4][CH:3]=1.[F-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[C:29]([O:30][CH2:31][CH2:32][OH:33])=[CH:28][CH:27]=[C:26]([C:34]#[CH:35])[C:25]=3[F:40])[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 76568160HCID 76568160, compound

Product 1

HCID 76567996HCID 76567996, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[2-fluoro-6-(2-hydroxy-ethoxy)-3-trimethylsilanylethynyl-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (50 mg, 0.08 mmol) prepared in example 184a in methanol (2 mL) was added KF (9.5 mg, 0.16 mmol) (Aldrich). The reaction mixture was stirred at room temperature for overnight. The solvent was removed and the residue was diluted with water and extracted with ethyl acetate. The organic layers were combined, washed with water, brine, dried over MgSO4, filtered and concentrated. The residue was purified with chromatography to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[3-ethynyl-2-fluoro-6-(2-hydroxy-ethoxy)-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as brown solid.

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified with chromatography

Sources & evidence

ORD record
ord-e578333d1a1544b1b94c2ed43b9f61bc
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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