Dimethyl Sulfoxide → 1-(4-Fluorophenyl)-2-(pyridin-4-yl)ethane-1,2-dione

HRID 1710686Notes

Reaction equation

HRID 1710686 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:27])[CH:19]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[OH:20])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O.C(Cl)Cl.O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:27])[C:19]([C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)=[O:20])=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 20674617HCID 20674617, compound

Product 1

HCID 117909921-(4-Fluorophenyl)-2-(pyridin-4-yl)ethane-1,2-dioneYield 94.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 21912085Dimethylsulfoxide-dichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

To a stirred cooled solution (−60° C.) of oxalyl chloride (3.55 mL, 40.8 mmol) in CH2Cl2 (16 mL) a solution of dimethyl sulfoxide (4.0 mL) in CH2Cl2 was added dropwise. Five minutes later a solution of 1-(4-fluorophenyl)-2-pyridin-4-ylethane-1,2-diol (4.0 g, 17 mmols) in DMSO/CH2Cl2 (32 mL/13 mL) was dropped. The mixture was allowed to stir for 30 min at −60° C. and then triethylamine (24 mL) was added. When the reaction reached room temperature was diluted with water and dichloromethane. The organic phases were washed with water and brine and dried (MgSO4). After removal of the solvent under vacuum, the resulting solid was triturated with hexane to afford the title compound as an orange solid (3.68 g, 94%).

Workup

  1. additionwas added dropwise
  2. customreached room temperature
  3. washThe organic phases were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customAfter removal of the solvent under vacuum
  6. customthe resulting solid was triturated with hexane

Sources & evidence

ORD record
ord-36193d5118e04232a291098ddccde78f
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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