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

HRID 403306Notes

Reaction equation

HRID 403306 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 a clear 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-2fcad731f42c4bcc820b327965c9d861
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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