Triethylamine → HCID 22611244、化合物

HRID 843811ノート

反応式

HRID 843811 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(N(CC)CC)C.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=[O:24]>O1CCCC1>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)=[O:24]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 788675-Aminoindole

生成物 1

HCID 22611244HCID 22611244、化合物収率 50.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2.09 gm (15.8 mMol) 5-amino-1H-indole in 20 mL tetrahydrofuran were added 2.6 mL (18.97 mMol) triethylamine and the solution was cooled in an ice bath. To the reaction mixture were then added dropwise 1.71 ml (17.4 mMol) 2-furoyl chloride. When this addition was complete the cooling bath was removed and the reaction mixture was stirred 1.5 hours at ambient temperature. At this point the reaction was diluted with water and extracted well with ethyl acetate. The organic solutions were combined and washed sequentially with water, 2N sodium hydroxide, water and saturated aqueous sodium chloride. The remaining organics were then dried over sodium sulfate and concentrated under reduced pressure to give a dark purple solid. The solid was subjected to flash chromatography, eluting with a gradient of dichloromethane containing 0-2% methanol. The recovered solid was crystallized from ethyl acetate to give 1.8 gm (50.3%) of 5-(2-furoyl)amino-1H-indole as pale purple crystals.

後処理

  1. temperaturethe solution was cooled in an ice bath
  2. additionWhen this addition
  3. customwas removed
  4. additionAt this point the reaction was diluted with water
  5. extractionextracted well with ethyl acetate
  6. washwashed sequentially with water, 2N sodium hydroxide, water and saturated aqueous sodium chloride
  7. dry with materialThe remaining organics were then dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a dark purple solid
  10. washeluting with a gradient of dichloromethane containing 0-2% methanol
  11. customThe recovered solid was crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-09d4af2a06c64e95b6964f7e58e493f7
出典データセット
uspto-grants-2002_04
特許番号
US06380201B1

反応ノート

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