Pyridine, hydrofluoride (1:1) → HCID 68815279, compound

HRID 732555Notes

Reaction equation

HRID 732555 reaction equation
[F:1][B-](F)(F)F.N#[O+].[CH3:8][O:9][C:10](=[O:34])[C:11]1[CH:23]=[C:22]([C:24]2([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)SCCS2)[CH:21]=[C:13]([C:14]([N:16]([CH3:20])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:12]=1.C1C=CN=CC=1.[FH:41]>ClCCl>[CH3:8][O:9][C:10](=[O:34])[C:11]1[CH:23]=[C:22]([C:24]([F:1])([F:41])[C:29]2[O:30][CH:31]=[CH:32][CH:33]=2)[CH:21]=[C:13]([C:14]([N:16]([CH3:20])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:12]=1

Participants

5

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 11137142Nitrilooxonium tetrafluoroborateHCID 86615015HCID 86615015, compound

Product 1

HCID 68815279HCID 68815279, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Under nitrogen and in a plastic vessel, dissolve nitrosonium tetrafluoroborate (84.8 μg, 0.72 mmol) and pyridinium poly(hydrogen fluoride) (70% hydrogen fluoride, 30% pyridine, 300 μL) in dichloromethane (2 mL) and cool to 0° C. Add dropwise 5-(2-furan-2-yl-[1,3]dithiolan-2-yl)-N-methyl-N-propyl-isophthalamic acid methyl ester in dichloromethane (1.5 mL) to the mixture, warm up to room temperature and stir for 2 h. Dilute the mixture with dichloromethane (20 mL) and filter the organic liquid though a pad of aluminum oxide and magnesium sulfate mixture. Concentrate the filtrate and purify (silica gel chromatography, 1:99 to 30:70 ethyl acetate:hexanes) to give the title compound (30%).

Workup

  1. temperaturewarm up to room temperature
  2. filtrationfilter the organic liquid though a pad of aluminum oxide and magnesium sulfate mixture
  3. concentrationConcentrate the filtrate
  4. custompurify (silica gel chromatography, 1:99 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-1e20638298a14eda8f2ac03579660884
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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