Ethyl Bromide → 2-Ethoxy-5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyridine

HRID 234709Notes

Reaction equation

HRID 234709 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.Br[CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:30]([O:18][C:11]1[CH:10]=[C:9]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=2)[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:13]([C:14]([F:15])([F:17])[F:16])[N:12]=1)[CH3:31]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 233552585-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)-2-oxo-pyridine

Product 1

HCID 102969342-Ethoxy-5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyridineYield 26.4%

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), 3,3 g of bromoethane, 0.2 g of potassium carbonate, and 5 mL of dimethyl formamide (DMF) was stirred for 20 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 methylene chloride/hexane to give 31 mg of solid: mp 168.5°-170.5° 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 methylene chloride/hexane

Sources & evidence

ORD record
ord-ff7c76f6387542bc8a3bd04a97cc127e
Source dataset
uspto-grants-1997_01
Patent number
US05596008

Reaction notes

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