Tetrabutylammonium Fluoride → HCID 46186188, compound

HRID 341287Notes

Reaction equation

HRID 341287 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl:19][C:20]1[CH:52]=[N:51][C:23]2[N:24](S(C3C=CC=CC=3)(=O)=O)[C:25]3[C:30]([C:22]=2[CH:21]=1)=[CH:29][C:28]([CH2:31][CH2:32][NH:33][C:34](=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[CH:27][CH:26]=3>C1COCC1>[Cl:19][C:20]1[CH:52]=[N:51][C:23]2[NH:24][C:25]3[C:30]([C:22]=2[CH:21]=1)=[CH:29][C:28]([CH2:31][CH2:32][NH:33][C:34](=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[CH:27][CH:26]=3

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 46186187HCID 46186187, compound

Product 1

HCID 46186188HCID 46186188, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At room temperature and under inert atmosphere, 1.0 M TBAF in THF (310 μL, 5 equiv.) was added a solution of 17 (30 mg, 0.061 mmol) in anhydrous THF (2.5 mL). The solution was refluxed for 2 h. The resulting mixture was then cautiously quenched at 0° C. with H2O. The mixture was extracted with EtOAc (3×10 mL). The resulting organic layers were dried over MgSO4, filtered, and solvents were removed under reduced pressure. The crude product was purified by flash chromatography (EtOAc) to afford R265 in 61% yield. 1H-NMR (300 MHz, DMSO-d6): δ 11.91 (bs, 1H), 8.65 (d, 1H, J=2.3 Hz), 8.61 (bt, 1H, J=5.5 Hz), 8.39 (d, 1H, J=2.3 Hz), 8.07 (bs, 1H), 7.82 (d, 1H, J=7.5 Hz), 7.54-7.37 (m, 5H), 3.55 (q, 2H, J=7.7 Hz), 2.98 (t, 2H, J=7.7 Hz); MS (ESI) m/z 350.2 [M+H+], 698.9 [2M+H+], 721.0 [2M+Na+], HRMS (ESI): Calcd for C20H16ClN3O: 350.1060. Found: 350.10631.

Workup

  1. temperatureThe solution was refluxed for 2 h
  2. customThe resulting mixture was then cautiously quenched at 0° C. with H2O
  3. extractionThe mixture was extracted with EtOAc (3×10 mL)
  4. dry with materialThe resulting organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customsolvents were removed under reduced pressure
  7. customThe crude product was purified by flash chromatography (EtOAc)
  8. customto afford R265 in 61% yield

Sources & evidence

ORD record
ord-566cdff7c60f4ffa9f39d1b7b4bd3dbe
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

Loading…