Ammonium Chloride → HCID 69670888, compound

HRID 1191686Notes

Reaction equation

HRID 1191686 reaction equation
[C:1]1([C:7]2[N:8]([CH2:28][C:29]3[N:34]=[C:33]([C:35]([O:37][CH3:38])=[O:36])[CH:32]=[CH:31][CH:30]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([CH2:16][O:17][Si](C(C)C)(C(C)C)C(C)C)=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[OH:17][CH2:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:28][C:29]1[N:34]=[C:33]([C:35]([O:37][CH3:38])=[O:36])[CH:32]=[CH:31][CH:30]=1)[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:15]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 69670820HCID 69670820, compound

Product 1

HCID 69670888HCID 69670888, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(2-phenyl-5-triisopropylsilanyloxymethylindol-1-ylmethyl)pyridine-2-carboxylate (77.0 mg) in tetrahydrofuran (0.728 mL) was added tetrabutylammonium fluoride (1.0 mol/L tetrahydrofuran solution, 0.190 mL) under cooling with ice. The mixture was stirred under cooling with ice for one hour and then at room temperature for additional 2 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (44.4 mg).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice for one hour
  3. extractionthis resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-dc136a98fca54f1382c197efeecb35ba
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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