Pyridine → 4-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-methylthiazole

HRID 357219Notes

Reaction equation

HRID 357219 reaction equation
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[C:22]([NH2:25])(=[S:24])[CH3:23].N1C=CC=CC=1>C(O)C>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:25]=[C:22]([CH3:23])[S:24][C:2]=2[C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2723949ThioacetamideHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 101722374-(4-Fluorophenyl)-5-(4-methylsulfonylphenyl)-2-methylthiazoleYield 31.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)-ethanone (1.10 g) in ethanol (15.0 mL) were added thioacetamide (0.266 g) and pyridine (0.300 mL). After refluxing for 2 h, the reaction mixture was extracted with EtOAc, 25% NH4OAc and purified by flash chromatography (50% EtOAc in hexane then 90% Et2O in hexane) to yield the title compound (0.320 g).

Workup

  1. temperatureAfter refluxing for 2 h
  2. extractionthe reaction mixture was extracted with EtOAc, 25% NH4OAc
  3. custompurified by flash chromatography (50% EtOAc in hexane

Sources & evidence

ORD record
ord-3403f308599a499b9ff0106056a4e395
Source dataset
uspto-grants-1998_11
Patent number
US05840746

Reaction notes

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