Triethylamine → HCID 22611244, compound

HRID 726013Notes

Reaction equation

HRID 726013 reaction equation
[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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 788675-Aminoindole

Product 1

HCID 22611244HCID 22611244, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-be3a7c9992d24375879cb2604f996a98
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

Loading…