Propargyl bromide → 5-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-(2-propynyloxy)-6-(trifluoromethyl)pyridine

HRID 234710Notes

Reaction equation

HRID 234710 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[CH:10][C:11](=[O:18])[NH:12][C:13]=2[C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1.[CH2:29](Br)[C:30]#[CH:31].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=3)=[CH:10][C:11]([O:18][CH2:31][C:30]#[CH:29])=[N:12][C:13]=2[C:14]([F:15])([F:17])[F:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 233552585-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)-2-oxo-pyridine

Product 1

HCID 102041985-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-(2-propynyloxy)-6-(trifluoromethyl)pyridineYield 46.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.11 g of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)-2-oxo-pyridine (step 5 of Example 1), 2.5 g of propargyl bromide, 0.3 g of potassium carbonate, and 5 mL of DMF was stirred for 60 hours and concentrated in vacuo. The residue was triturated with water and extracted with methylene chloride. The methylene chloride extract was dried over MgSO4 and filtered through silica gel. The filtrate was reconcentrated in vacuo and the residue was crystallized from ether/hexane to give 56 mg of white solid: mp 138°-139° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with water
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered through silica gel
  7. customthe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-48bb3ec879e34d8cae23697c523b7e97
Source dataset
uspto-grants-1997_01
Patent number
US05596008

Reaction notes

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