Sodium Bicarbonate → 2-Ethyl-5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazole

HRID 1268731Notes

Reaction equation

HRID 1268731 reaction equation
Br.Br[CH:3]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([F:19])[CH:14]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=1)=O.[C:20]([NH2:24])(=[S:23])[CH2:21][CH3:22].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:21]([C:20]1[S:23][C:3]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([F:19])[CH:14]=2)=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[CH:7]=2)[N:24]=1)[CH3:22]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2760628PropanethioamideHCID 116034772-Bromo-2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone hydrocbromide

Product 1

HCID 99008852-Ethyl-5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazoleYield 38.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone hydrobromide (11 g, 29 mmol) and thiopropionamide (2.7 g, 30 mmol) in N,N-dimethylformamide (30 mL) was stirred at room temperature for 14 hrs. Aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1) to give the title compound (3.3 g, yield 38%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1)

Sources & evidence

ORD record
ord-6ca5d3d7dd474f2ea633d55d989be21e
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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