1-Amino-2-propanol → 3-Methyl-6-(2-thienyl)-4,5,6,7-tetrahydroindol-4-one

HRID 1700444ノート

反応式

HRID 1700444 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:11][C:10](=O)[CH2:9][C:8](=[O:13])[CH2:7]1.[NH2:14][CH2:15][CH:16](O)[CH3:17]>O1CCCC1>[CH3:17][C:16]1[C:9]2[C:8](=[O:13])[CH2:7][CH:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH2:11][C:10]=2[NH:14][CH:15]=1

参加物

4

反応物 2

HCID 41-Amino-2-propanolHCID 5736855-(2-Thienyl)cyclohexane-1,3-dione

生成物 1

HCID 183177703-Methyl-6-(2-thienyl)-4,5,6,7-tetrahydroindol-4-one収率 30.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
150 °C

実験手順

A mixture of 5-thienylcyclohexane-1,3-dione (2.0 g), 3-aminopropan-2-ol (1.0 g), molecular sieves 4A (12 g) and tetrahydrofuran (30 ml) was refluxed for 12 hours and cooled, and insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in dimethylformamide (40 ml). To the mixture were added 2-bromomesitylene (2.1 g), tetrakistriphenylphosphine palladium (0.30 g) and potassium carbonate (2.8 g), and the mixture was stirred at 150° C. for 7 hours and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give 3-methyl-6-(2-thienyl)-4,5,6,7-tetrahydroindol-4-one (0.72 g).

後処理

  1. temperaturewas refluxed for 12 hours
  2. temperaturecooled
  3. filtrationinsoluble materials were filtered off
  4. customUnder reduced pressure, the solvent was evaporated
  5. dissolutionthe residue was dissolved in dimethylformamide (40 ml)
  6. additionTo the mixture were added 2-bromomesitylene (2.1 g), tetrakistriphenylphosphine palladium (0.30 g) and potassium carbonate (2.8 g)
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. washthe solution was washed with sodium hydrogen carbonate solution, water and saturated brine
  10. dry with materialdried with magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-41ea5c367f9f4eae8aad2fef0027e99a
出典データセット
uspto-grants-2002_02
特許番号
US06350749B1

反応ノート

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