Water → HCID 59296184, compound

HRID 2233589Notes

Reaction equation

HRID 2233589 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10][OH:11])[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[C:28]([F:34])[CH:27]=1.O>CN(C)C=O>[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10][O:11][CH2:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[C:28]([F:34])[CH:27]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27784664-Cyano-3-fluorobenzyl bromideHCID 58934102HCID 58934102, compound

Product 1

HCID 59296184HCID 59296184, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.255 g of [4-butyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl]-methanol in 25 ml of dimethylformamide was added 0.286 g of a 60% dispersion of sodium hydride in mineral oil. After stirring for 15 minutes, 3 g of 4-bromomethyl-2-fluoro-benzonitrile was added. The resulting mixture was stirred at room temperature overnight, then poured into water, extracted with diisopropyl ether. The combined organic extracts were washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (heptane 95/ethyl acetate 5) to give 0.6 g of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxymethyl]-2-fluoro-benzonitrile, which was transformed into 3-{4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxymethyl]-2-fluoro-phenyl}-4H-[1,2,4]oxadiazol-5-one according to the method described in example 1.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. extractionextracted with diisopropyl ether
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel (heptane 95/ethyl acetate 5)

Sources & evidence

ORD record
ord-d25ea42749db44b88d754e29e5673151
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

Loading…