Selectfluor → HCID 59255049, compound

HRID 1809357Notes

Reaction equation

HRID 1809357 reaction equation
[CH:1]([N:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]1=[O:16])([CH3:3])[CH3:2].[F:17][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>C(#N)C>[F:17][C:8]1[CH:7]=[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5](=[O:16])[N:4]([CH:1]([CH3:2])[CH3:3])[C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 59255053HCID 59255053, compound

Product 1

HCID 59255049HCID 59255049, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 1-isopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate as prepared in Example 1(5) (2.23 g, 10.0 mmol) and 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (3.76 g, 10.6 mmol) in acetonitrile (80 mL) was stirred at room temperature for 16 h. The mixture was quenched with water (300 mL), and extracted with ethyl acetate (100 mL×4). The combined organic layers were washed with water (100 mL×6), brine (100 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (v/v=2/1˜1/1) to give 572 mg (24%) of the title compound as a yellow solid.

Workup

  1. customThe mixture was quenched with water (300 mL)
  2. extractionextracted with ethyl acetate (100 mL×4)
  3. washThe combined organic layers were washed with water (100 mL×6), brine (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (v/v=2/1˜1/1)

Sources & evidence

ORD record
ord-3d3989319bb34822a18506d51801f5d4
Source dataset
uspto-grants-2013_01
Patent number
US08362038B2

Reaction notes

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