Pyridine → 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

HRID 533608

反応式

HRID 533608 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH:8][CH3:9])=[N:6][CH:7]=1.[CH2:11]([S:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[C:16](O)=O)[CH3:12].CCN=C=NCCCN(C)C.N1C=CC=CC=1>C1C=CC2N(O)N=NC=2C=1.O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:16]([C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[S:13][CH2:11][CH3:12])[N:8]([CH3:9])[C:5]2=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 151940325-Bromo-N2-methylpyridine-2,3-diamine

生成物 1

HCID 679820336-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine収率 49.7%

試薬・触媒・溶媒 2

HCID 757711-Hydroxybenzotriazole触媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

A mixture of 5-bromo-N2-methylpyridin-2,3-diamine (0.70 g), 2-ethylsulfanylbenzoic acid (0.66 g), WSC (0.80 g), HOBt (23 mg), and pyridine (20 ml) was stirred under reflux at 120° C. for 30 minutes. After the reaction mixture was allowed to stand overnight, the mixture was stirred under reflux at 120° C. for 9.5 hours again. Into the reaction mixture cooled to room temperature, water was poured under ice-cooling, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. A mixture of the resulting residue and acetic anhydride (7 ml) was stirred under reflux at 140° C. for 1 hour. Aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature to neutralize, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.60 g of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 42).

後処理

  1. stirringthe mixture was stirred
  2. temperatureunder reflux at 120° C. for 9.5 hours again
  3. temperatureInto the reaction mixture cooled to room temperature
  4. temperaturecooling
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionA mixture of the resulting residue and acetic anhydride (7 ml)
  10. stirringwas stirred
  11. temperatureunder reflux at 140° C. for 1 hour
  12. additionAqueous sodium hydroxide solution was added to the reaction mixture
  13. temperaturecooled to room temperature
  14. extractionextracted with ethyl acetate
  15. washThe organic layer was washed with water and saturated brine
  16. dry with materialdried over sodium sulfate
  17. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6605ff75e1b54fa88853c38aa4360b3c
出典データセット
uspto-grants-2014_10
特許番号
US08853238B2

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