Bromine → 5-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-2-[4-(methylthio)phenyl]-1,3-thiazole

HRID 2212342ノート

反応式

HRID 2212342 の反応式
BrBr.[F:3][C:4]1[CH:9]=[C:8]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)=O)[CH:7]=[CH:6][N:5]=1.[CH3:20][S:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH2:28])=[S:27])=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[F:3][C:4]1[CH:9]=[C:8]([C:10]2[S:27][C:26]([C:25]3[CH:29]=[CH:30][C:22]([S:21][CH3:20])=[CH:23][CH:24]=3)=[N:28][C:11]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)[CH:7]=[CH:6][N:5]=1

参加物

6

反応物 4

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 30033144-(Methylthio)thiobenzamideHCID 115431572-(2-Fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone

生成物 1

HCID 101573605-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-2-[4-(methylthio)phenyl]-1,3-thiazole収率 23%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Bromine (2.7 mL, 52 mmol) was added to a solution of 2-(2-fluoro-4-pyridyl)-1-(3-methylphenyl)ethanone (12 g, 53 mmol) in acetic acid (90 mL) and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated. This residue was dissolved in N,N-dimethylformamide (60 mL), 4-(methylthio)thiobenzamide (9.6 g, 52 mmol) was added and the mixture was stirred at room temperature for 15 hours. A saturated aqueous solution of sodium hydrogencarbonate (100 mL) 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 distilled off. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 4:1) to obtain 4.7 g (yield 23%) of the title compound.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThis residue was dissolved in N,N-dimethylformamide (60 mL)
  3. stirringthe mixture was stirred at room temperature for 15 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 4:1)

出典と根拠

ORDレコード
ord-37b8be9e91674ff8825d2288832fa7e0
出典データセット
uspto-grants-2006_09
特許番号
US07101899B1

反応ノート

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