Pyridine, hydrofluoride (1:1) → HCID 59625893, compound

HRID 2365370Notes

Reaction equation

HRID 2365370 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.C1C=CN=CC=1.[FH:28].[C:29]1([C:35]2([C:40]3[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][CH:41]=3)SCCS2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[F:28][C:35]([F:21])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:40]1[CH:49]=[CH:48][C:43]([C:44]([O:46][CH3:47])=[O:45])=[CH:42][CH:41]=1

Participants

6

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 2724933SelectfluorHCID 59625898HCID 59625898, compound

Product 1

HCID 59625893HCID 59625893, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 178435160HCID 178435160, compoundSolvent

Conditions

Temperature
0 °C

Procedure

Selectfluor (1.07 mmol, 381 mg) and HF-pyridine reagent (1.5 mL, HF: Pyridine=70:30 wt %) were dissolved in CH2Cl2 (4 mL) in a polyethylene bottle and cooled to 0° C. A solution of 64b (0.512 mmol, 162 mg) in CH2Cl2 (2 mL) was slowly added and the mixture was stirred for 45 min at room temperature. When TLC indicated the consumption of all 64b, the reaction was diluted with CH2Cl2. The combined organics were dried over anhydrous Na2SO4 and concentrated. The crude product was purified by flash column chromatography (silica gel, 5% EtOAc/hexanes) to afford compound 64c as a clear oil.

Workup

  1. customthe consumption of all 64b
  2. additionthe reaction was diluted with CH2Cl2
  3. dry with materialThe combined organics were dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash column chromatography (silica gel, 5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-81b7a4bcc9364d1881a805463650dcde
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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