Tetrabutylammonium Fluoride → HCID 86703321, compound

HRID 2410006Notes

Reaction equation

HRID 2410006 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:19]3[CH:20]=[N:21][CH:22]=[N:23][CH:24]=3)[N:9]2C(OC(C)(C)C)=O)=[CH:5][CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:19]3[CH:20]=[N:21][CH:22]=[N:23][CH:24]=3)[NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86703320HCID 86703320, compound

Product 1

HCID 86703321HCID 86703321, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 6-methoxy-2-pyrimidin-5-yl-1H-indole-1-carboxylate (295 mg) in tetrahydrofuran (2.27 mL) was added tetrabutylammonium fluoride (about 1.0 mol/L tetrahydrofuran solution, 3.63 mL) at room temperature, and the mixture was heated under reflux for 30 hours. The reaction mixture was left to be cooled, diluted with ethyl acetate, and then washed with saturated brine. The organic layer was 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 (186 mg). 1H-NMR (CDCl3) δ ppm: 3.88 (3H, s), 6.84 (1H, dd, J=2.3, 8.8 Hz), 6.88-6.95 (2H, m), 7.54 (1H, d, J=8.8 Hz), 8.20-8.52 (1H, br), 8.99 (2H, s), 9.11 (1H, s). ESI-MS (m/z): 226 (M+H)+

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 hours
  3. waitThe reaction mixture was left
  4. temperatureto be cooled
  5. washwashed with saturated brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-c3b2539f99194dc89c9f260e7f3856f9
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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