Chloroform → Tert-butyl 6-chloro-3[(4-methoxyphenyl)sulfanyl]pyridine-2-carboxylate

HRID 1798968Notes

Reaction equation

HRID 1798968 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:17]1[C:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:19][C:20]([Cl:23])=[CH:21][CH:22]=1.C(Cl)(Cl)Cl>CN(C)C=O>[Cl:23][C:20]1[N:19]=[C:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([S:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 23092542HCID 23092542, compound

Product 1

HCID 87354225Tert-butyl 6-chloro-3[(4-methoxyphenyl)sulfanyl]pyridine-2-carboxylateYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methoxythiophenol (0.927 ml; 7.55 mmol) and 1.14 g (8.26 mmol) of potassium carbonate were added, at room temperature, to a solution (70 ml) of 1.70 g (6.86 mmol) of the resulting ester compound in N,N-dimethylformamide followed by stirring for 1 hour. Chloroform was added to the reaction solution followed by washing with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous saline solution, drying and concentrating in vacuo. The resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate 9:1) to give 743 mg (yield: 31%) of tert-butyl 6-chloro-3-(4-methoxy-phenylsulfanyl)-2-pyridinecarboxylate as a colorless oily substance.

Workup

  1. washby washing with a saturated aqueous solution of sodium hydrogen carbonate
  2. customa saturated aqueous saline solution, drying
  3. concentrationconcentrating in vacuo
  4. customThe resulting residue was purified by a silica gel column chromatography (hexane:ethyl acetate 9:1)

Sources & evidence

ORD record
ord-5fb8bc53f2d7485aa8cee39fc818683e
Source dataset
uspto-grants-2013_01
Patent number
US08344003B2

Reaction notes

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