Potassium Carbonate → 2-(5-(3,4-dimethoxy-5-nitrophenyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine

HRID 61995

反応式

HRID 61995 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([N+:24]([O-:26])=[O:25])[C:21]=1[O:22][CH3:23])[CH:17]=O.[N+:27]([CH2:29]S(C1C=CC(C)=CC=1)(=O)=O)#[C-:28].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(O)(=O)C.CO.COCCOC>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:17]2[N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:10])[F:11])=[CH:8][N:7]=3)[CH:29]=[N:27][CH:28]=2)[CH:19]=[C:20]([N+:24]([O-:26])=[O:25])[C:21]=1[O:22][CH3:23]

参加物

9

反応物 4

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 108675653,4-Dimethoxy-5-nitrobenzaldehyde

生成物 1

HCID 687019682-(5-(3,4-dimethoxy-5-nitrophenyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a stirred solution of 5-(trifluoromethyl)pyridin-2-amine (0.405 g, 2.5 mmol) in a mixture of ethanol (12.5 mL) and acetic acid (0.25 mL) at room temperature was added 3,4-dimethoxy-5-nitrobenzaldehyde (0.53 g, 2.5 mmol). The reaction was heated at reflux temperature for two hours then ethanol was evaporated. The oily residue was dissolved in a mixture of methanol (17 mL) and 1,2-dimethoxyethane (7.5 mL), whereupon 1-(isocyanomethylsulfonyl)-4-methylbenzene (TOSMIC) (0.73 g, 3.75 mmol) and potassium carbonate (0.69 g, 5 mmol) were added in one portion. The resulting mixture was stirred at reflux temperature for 3 hours. The reaction was evaporated to dryness, and then taken up in dichloromethane (50 ml). The organic phase was washed with water (50 mL) and then dried over anhydrous magnesium sulphate, filtered and evaporated to leave brown oil. Column chromatography over silica gel (petroleum ether-ethyl acetate 9:1) gave 2-(5-(3,4-dimethoxy-5-nitrophenyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine, 0.542 g (55%).

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux temperature for two hours
  3. customethanol was evaporated
  4. additionwere added in one portion
  5. temperatureat reflux temperature for 3 hours
  6. customThe reaction was evaporated to dryness
  7. washThe organic phase was washed with water (50 mL)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customto leave brown oil

出典と根拠

ORDレコード
ord-b834e390d6be47aabc37cf6474b36fa1
出典データセット
uspto-grants-2016_09
特許番号
US09446012B2

関連ノート

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