Triethylamine → HCID 22611244, 화합물

HRID 1738007노트

반응식

HRID 1738007 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 788675-Aminoindole

생성물 1

HCID 22611244HCID 22611244, 화합물수율 50.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f8f1261b415145399d6c774074004647
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962473

반응 노트

불러오는 중…