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

HRID 2038426Notes

Reaction equation

HRID 2038426 reaction equation
F[B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+]([F:21])(CC1)CC2.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

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor) (381 mg, 1.07 mmol) 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 compound 18b (162 mg, 0.512 mmol) in CH2Cl2 (2 mL) was slowly added and the mixture was stirred for 45 min at room temperature. The solution was extracted with CH2Cl2, and the combined organics were dried over anhydrous Na2SO4 and concentrated. A crude product was purified by flash column chromatography (silica gel, 5% EtOAc/hexanes) to afford compound 18c as aclear oil.

Workup

  1. extractionThe solution was extracted with CH2Cl2
  2. dry with materialthe combined organics were dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customA crude product was purified by flash column chromatography (silica gel, 5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1624bf00725943d0ad7e40d74cb69c1a
Source dataset
uspto-grants-2013_11
Patent number
US08575363B2

Reaction notes

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