Cesium fluoride → HCID 178450303, compound

HRID 1942224Notes

Reaction equation

HRID 1942224 reaction equation
[CH:1]1([O:4][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[N:11]=[C:10]([C:15]([C:20]2[N:24](COCC[Si](C)(C)C)[N:23]=[N:22][CH:21]=2)([OH:19])[CH:16]([CH3:18])[CH3:17])[CH:9]=[CH:8]3)[CH2:3][CH2:2]1.[F-].[Cs+].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][CH:14]=2)[N:11]=[C:10]([C:15]([C:20]2[N:24]=[N:23][NH:22][CH:21]=2)([OH:19])[CH:16]([CH3:18])[CH3:17])[CH:9]=[CH:8]3)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 2724141Tetrabutylammonium FluorideHCID 69281306HCID 69281306, compound

Product 1

HCID 178450303HCID 178450303, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(6-cyclopropoxyquinolin-2-yl)-2-methyl-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,3-triazol-5-yl)propan-1-ol (AR) (0.35 g, 0.77 mmol) in THF (5 mL) was added CsF (0.42 g, 3.08 mmol) followed by TBAF (1 mL, 0.77 mmol, 1M solution in THF) at RT and stirred under reflux for 12 h under inert atmosphere. After consumption of the starting material (by TLC), the reaction mixture was quenched with water (20 mL) and extracted with EtOAc (3×30 mL). The combined organic layer was washed with water, brine and dried over anhydrous Na2SO4 and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography using 30% EtOAc/hexane as eluent to afford 8 (85 mg, 0.26 mmol, 33%) as off-white solid. 1H NMR (500 MHz, CDCl3): δ 11.82-11.60 (br s, 1H), 8.08 (d, J=9.0 Hz, 1H), 7.97 (d, J=10.0 Hz, 1H), 7.81 (br s, 2H), 7.38-7.36 (m, 2H), 6.62 (s, 1H), 3.85-3.84 (m, 1H), 2.82-2.80 (m, 1H), 0.98 (d, J=7.0 Hz, 3H), 0.87-0.83 (m, 4H), 0.64 (d, J=7.0 Hz, 3H). HPLC: 98.3%. MS (ESI): m/z 325.9 [M++1].

Workup

  1. temperatureunder reflux for 12 h under inert atmosphere
  2. customAfter consumption of the starting material (by TLC)
  3. customthe reaction mixture was quenched with water (20 mL)
  4. extractionextracted with EtOAc (3×30 mL)
  5. washThe combined organic layer was washed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained crude product
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b50660fbaa7846f9a0cc9c30296d1916
Source dataset
uspto-grants-2013_03
Patent number
US08389543B2

Reaction notes

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