Potassium Fluoride → HCID 15811458, compound

HRID 868769Notes

Reaction equation

HRID 868769 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][Si](C)(C)C)=[CH:15][N:14]=2)=[N:11][CH:12]=1)(C)C.[F-].[K+]>CO.C1COCC1>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:9]=[CH:8][C:7]([C:6]#[CH:5])=[CH:12][N:11]=2)=[N:14][CH:15]=1)#[CH:20]

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 5247662HCID 5247662, compound

Product 1

HCID 15811458HCID 15811458, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4 (390 mg, 1.12 mmol) was dissolved in a mixture of 40 ml MeOH and 10 ml THF; then KF powder (400 mg, 6.88 mmol) was added and the solution was stirred at room temperature overnight. Subsequently, the solvents were removed under reduced pressure. The residue was redissolved in 200 ml CH2Cl2 and washed four times with 100 ml H2O each, in order to remove inorganic salts. The organic phase was dried over Na2SO4, concentrated under reduced pressure and purified by silica flash column chromatography (eluent: CH2Cl2) to yield a colorless powder of 204 mg (1.0 mmol, 81%) pure 5. 1H NMR (CDCl3, 250 MHz): δ=8.76 (d, 2H, JHH=1.0 Hz, bpy-H), 8.39 (d, 2H, JHH=6.0 Hz, bpy-H), 7.90 (dd, 2H, JHH=1.1 Hz, 5.1 Hz, bpy-H), 3.31 (s, 2H, bpy-CCH).

Workup

  1. customSubsequently, the solvents were removed under reduced pressure
  2. dissolutionThe residue was redissolved in 200 ml CH2Cl2
  3. washwashed four times with 100 ml H2O each, in order
  4. customto remove inorganic salts
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica flash column chromatography (eluent: CH2Cl2)
  8. customto yield a colorless powder of 204 mg (1.0 mmol, 81%) pure 5

Sources & evidence

ORD record
ord-1513561857dc4ebeb902cb5959c561aa
Source dataset
uspto-grants-2015_03
Patent number
US08968886B2

Reaction notes

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