Potassium Carbonate → HCID 67179275, compound

HRID 1676965Notes

Reaction equation

HRID 1676965 reaction equation
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C[O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([S:17][C:14]2[CH:15]=[CH:16][C:11]([C:10]([OH:18])=[O:9])=[CH:12][CH:13]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 707143-IodopyridineHCID 237573Methyl 4-sulfanylbenzoate

Product 1

HCID 67179275HCID 67179275, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-iodopyridine (823 mg, 4.01 mmol), methyl-4-mercaptobenzoate (500 mg, 2.97 mmol), potassium carbonate (677 mg, 4.90 mmol), and copper dust (4 mg, 0.653 mmol) in dimethylformamide (10 mL) are heated to reflux temperature for 18 h. The heat is removed and the reaction is filtered through Celite® with dichloromethane. The filtrate is concentrated in vacuo and the residue is recrystallized from ether and hexane to obtain 689 mg (99%) of the title compound. MS (ES+) m/e 232.0 (M+1)+.

Workup

  1. temperatureare heated
  2. temperatureto reflux temperature for 18 h
  3. customThe heat is removed
  4. filtrationthe reaction is filtered through Celite® with dichloromethane
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe residue is recrystallized from ether and hexane

Sources & evidence

ORD record
ord-a514f034cd1c4700a88a143a5dcbc4b9
Source dataset
uspto-grants-2011_08
Patent number
US08008296B2

Reaction notes

Loading…