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

HRID 1727354Notes

Reaction equation

HRID 1727354 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.C1([CH2:26][CH2:27][C:28]([NH2:30])=[S:29])C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:27]([C:28]1[S:29][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:30]=1)[CH3:26]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 51507353-PhenylpropanethioamideHCID 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 for 14 hours at room temperature. Aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and extracted with ethyl acetate. The extracts were washed with water, dried, then, the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1) to obtain a title compound (3.3 g, yield 38%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. customdried
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1)

Sources & evidence

ORD record
ord-03afc7c62ea542f390f7b9983a6a1502
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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