Sodium Bicarbonate → 4-[2-(4-Fluorophenyl)-4-(3-methylphenyl)-1,3-thiazol-5-YL]-2-pyridylamine

HRID 2212339Notes

Reaction equation

HRID 2212339 reaction equation
Br.[NH2:2][C:3]1[CH:8]=[C:7]([CH:9](Br)[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)=O)[CH:6]=[CH:5][N:4]=1.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[S:26])=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]2[S:26][C:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([NH2:2])[CH:8]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=3)[N:27]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 7372234-FluorothiobenzamideHCID 219642042-(2-Amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromide

Product 1

HCID 219642494-[2-(4-Fluorophenyl)-4-(3-methylphenyl)-1,3-thiazol-5-YL]-2-pyridylamineYield 84.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2-Amino-4-pyridyl)-2-bromo-1-(3-methylphenyl)ethanone hydrobromide (5.0 g, 13 mmol) was dissolved in N,N-dimethylformamide (40 mL), to the solution was added 4-fluorothiobenzamide (2.1 g, 13 mmol) and the mixture was stirred at room temperature for 16 hours. A saturated aqueous solution of sodium hydrogencarbonate (200 mL) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The residue was recrystallized from ethanol to obtain 3.9 g (11 mmol, yield 83%) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe extract was dried
  3. distillationthe solvent was distilled off
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-30767424729f44348f269dff9b0919c0
Source dataset
uspto-grants-2006_09
Patent number
US07101899B1

Reaction notes

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