Potassium Fluoride → HCID 24864648, compound

HRID 1479245Notes

Reaction equation

HRID 1479245 reaction equation
C([CH:5]([O:27][C:28]1[CH:29]=[N:30][NH:31][C:32](=[O:35])[C:33]=1[Cl:34])[C:6]1[CH:26]=[CH:25][C:9]([O:10][CH2:11][CH2:12][CH2:13]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:8][CH:7]=1)(C)(C)C.[F-:36].[K+]>C(#N)C>[C:6]([N:31]1[C:32](=[O:35])[C:33]([Cl:34])=[C:28]([O:27][CH2:5][C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH2:13][F:36])=[CH:25][CH:26]=2)[CH:29]=[N:30]1)([CH3:26])([CH3:7])[CH3:5]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 87268750HCID 87268750, compound

Product 1

HCID 24864648HCID 24864648, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a scintillation vial containing a suspension of Example 4F (4.5 mg, 8.64×10−3 mmol) in anhydrous acetonitrile (0.25 mL) was added a solution of potassium fluoride (1.6 mg, 4.07×10−2 mmol) and kryptofix (15.0 mg, 4.07×10−2 mmol) in anhydrous acetonitrile (0.25 mL). The vial was capped and lowered into a 90° C. oil bath. The reaction was allowed to stir for 40 minutes. The reaction was cooled and concentrated under reduced pressure. Preparatory thin layer chromatography [silica gel; eluent pentane-ethyl acetate (3:2)] provided the desired product (0.8 mg, 25%). 1H (CDCl3) δ(ppm): 1.62 (s, 9H); 2.14-2.20 (m, 2H); 4.09-4.11 (m, 2H); 4.60 (t, 1H); 4.68 (t, 1H); 5.24 (s, 2H); 6.92 (d, 2H); 7.32 (d, 2H); 7.72 (s, 1H); 19F (CDCl3, CFCl3 as internal standard) δ(ppm): −222.66 (t of t, J=28.2, −50.4).

Workup

  1. customThe vial was capped
  2. customlowered into a 90° C.
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-824f9468be934f90a51a571015f4b803
Source dataset
uspto-grants-2016_08
Patent number
US09408927B2

Reaction notes

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