Dimethylformamide → HCID 22004821, compound

HRID 324614Notes

Reaction equation

HRID 324614 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]#[CH:9].CN(C)C=O.[F:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][C:25]=1[OH:26])[CH:22]([CH2:27][CH2:28][NH:29][C:30](=[O:33])[CH2:31][CH3:32])[CH2:21][CH2:20]2>O>[F:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][C:25]=1[O:26][CH2:9][C:8]#[CH:7])[CH:22]([CH2:27][CH2:28][NH:29][C:30](=[O:33])[CH2:31][CH3:32])[CH2:21][CH2:20]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 22004835HCID 22004835, compound

Product 1

HCID 22004821HCID 22004821, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Potassium carbonate (1.37 g, 9.95 mmols) and propargyl bromide (2.4 g, 19.9 mmols) were added to a dimethylformamide (10 ml) solution of N-[2-(5-fluoro-6-hydroxyindan-1-yl)ethyl]propionamide (0.5 g, 1.99 mmols) and stirred at 120° C. for 2 hours. The reaction solution was poured into water, and the organic substance was extracted out with ethyl acetate. The extract was washed with a saturated saline solution and water and then dried with anhydrous magnesium sulfate, and the solvent was removed through distillation under reduced pressure. The resulting residue was purified through silica-gel column chromatography (ethyl acetate) to obtain 0.56 g (yield: 97%) of the target compound.

Workup

  1. extractionthe organic substance was extracted out with ethyl acetate
  2. washThe extract was washed with a saturated saline solution and water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was removed through distillation under reduced pressure
  5. customThe resulting residue was purified through silica-gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-7537dd70ff26441fb07f23144dbcbe71
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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