Cesium fluoride → HCID 178503099, compound

HRID 467841Notes

Reaction equation

HRID 467841 reaction equation
[CH3:1][CH:2]([CH3:30])[C:3]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([S:28][CH3:29])[CH:24]=2)[N:19]=1)([C:5]1[N:9](COCC[Si](C)(C)C)[N:8]=[N:7][CH:6]=1)[OH:4].[F-].[Cs+].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][CH:2]([CH3:30])[C:3]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([S:28][CH3:29])[CH:24]=2)[N:19]=1)([C:5]1[N:9]=[N:8][NH:7][CH:6]=1)[OH:4]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 2724141Tetrabutylammonium FluorideHCID 69281289HCID 69281289, compound

Product 1

HCID 178503099HCID 178503099, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 2-methyl-1-(6-(methylthio)quinolin-2-yl)-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,3-triazol-5-yl)propan-1-ol (AL) (1 g, 2.25 mmol) in THF (20 mL) was added CsF (1.02 g, 6.75 mmol) followed by TBAF (2.24 mL, 2.25 mmol) (1M solution in THF) at RT under inert atmosphere. The reaction mixture was heated to 80° C. and stirred for 16 h. After consumption of the starting material (by TLC), the reaction mixture was diluted with water (30 mL) and extracted with EtOAc (3×30 mL). The combined organic layer was washed with water, 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 7 (70 mg, 0.22 mmol, 9.9%). 1H NMR (500 MHz, CDCl3): δ 11.65-11.63 (br s, 1H), 8.04 (d, J=8.5 Hz, 1H), 7.95 (d, J=9.0 Hz, 1H), 7.80 (br s, 2H), 7.59 (dd, J=2.0, 9.0 Hz, 1H), 7.52-7.51 (m, 1H), 6.54 (s, 1H), 2.82-2.80 (m, 1H), 2.58 (s, 3H), 0.97 (d, J=6.5 Hz, 3H), 0.63 (d, f=6.5 Hz, 3H). HPLC: 95.12%. MS (ESI): m/z 315 [M++1].

Workup

  1. customAfter consumption of the starting material (by TLC)
  2. additionthe reaction mixture was diluted with water (30 mL)
  3. extractionextracted with EtOAc (3×30 mL)
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-96511aad4a1b4eedb012ea3a5bde8397
Source dataset
uspto-grants-2014_01
Patent number
US08623892B2

Reaction notes

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