Triethylamine → HCID 22611379, compound

HRID 726014Notes

Reaction equation

HRID 726014 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH3:18])[CH2:13][CH2:12]1.C(N(CC)CC)C.[O:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](Cl)=[O:32]>O1CCCC1.CN(C)C=O>[O:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH3:18])[CH2:13][CH2:12]1)=[O:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 22611432HCID 22611432, compound

Product 1

HCID 22611379HCID 22611379, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.780 gm (3.2 mMol) 5-amino-3-(1-ethylpiperidin-4-yl)-1H-indole in 10 mL tetrahydrofuran and 10 mL dimethylformamide were added 0.536 mL (3.85 mMol) triethylamine followed by the dropwise addition of 0.348 mL (3.5 mMol) 2-furoyl chloride. After 18 hours the reaction mixture was cooled in an ice bath. The reaction mixture was the partitioned between 100 mL ethyl acetate and 100 mL 2N sodium hydroxide. The phases were separated and the aqueous extracted again with ethyl acetate. Organic extracts were combined and washed sequentially with 2N sodium hydroxide, water and saturated aqueous sodium chloride. The remaining organics were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to radial chromatography (2 mm silica), eluting with 100:10:1 dichloromethane:methanol:ammonium hydroxide. Fractions containing product were combined and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/hexane to give 0.789 gm (73.1%) of the title compound as an off-white solid.

Workup

  1. temperatureAfter 18 hours the reaction mixture was cooled in an ice bath
  2. custompartitioned between 100 mL ethyl acetate and 100 mL 2N sodium hydroxide
  3. customThe phases were separated
  4. extractionthe aqueous extracted again with ethyl acetate
  5. washwashed sequentially with 2N sodium hydroxide, water and saturated aqueous sodium chloride
  6. dry with materialThe remaining organics were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluting with 100:10:1 dichloromethane
  9. additionFractions containing product
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-9d17673d614645cba157d7db3fb75db7
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

Loading…