Triethylamine → HCID 22506867, compound

HRID 985596Notes

Reaction equation

HRID 985596 reaction equation
Cl.[C:2]([C:6]1[C:7]2[CH2:8][C:9]([CH3:22])([CH3:21])[NH:10][C:11]=2[C:12]([CH3:20])=[C:13]2[CH2:17][C:16]([CH3:19])([CH3:18])[O:15][C:14]=12)([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])O.[Na+].C(N(CC)CC)C.[F:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1>C1COCC1>[C:2]([C:6]1[C:7]2[CH2:8][C:9]([CH3:22])([CH3:21])[N:10]([C:40](=[O:41])[C:39]3[CH:43]=[CH:44][C:36]([F:35])=[CH:37][CH:38]=3)[C:11]=2[C:12]([CH3:20])=[C:13]2[CH2:17][C:16]([CH3:19])([CH3:18])[O:15][C:14]=12)([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 516892Sodium Bicarbonate2×HCID 22506882HCID 22506882, compound

Product 1

HCID 22506867HCID 22506867, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-tert-Butyl-3, 5, 6, 7-tetrahydro-2,2,4,6,6-pentamethyl-2H-furo[2,3-f]indole hydrochloride (715.8 mg, 2.21 mmol) was suspended in THF (20 ml). To the mixture was added a saturated aqueous solution of sodium hydrogen carbonate (50 ml) and stirred for 1 hour at room temperature. After extracting with isopropyl ether followed by drying over magnesium sulfate, the solvent was removed under reduced pressure. The residue was dissolved in THF (20 ml). To the solution were added triethylamine (0.35 ml, 2.51 mmol) and p-fluorobenzoyl chloride (371.8 mg, 2.34 mmol) and stirred at room temperature for 5 hours. To the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1) to obtain 417 mg of the title compound as an amorphous powder.

Workup

  1. extractionAfter extracting with isopropyl ether
  2. dry with materialby drying over magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in THF (20 ml)
  5. stirringstirred at room temperature for 5 hours
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-0c83d68f33b642979685e536af500c70
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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