Reaction #47843

Reaction equation

1-Bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

benzylamine

sodium iodide

→

titled compound

Yield 44.0%

1-benzylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic Acid Ethyl Ester

Yield 44.0%

Solvents

THF

Conditions

Workup

1. 1
   Temperatureby refluxing for 6 hrs
2. 2
   WashThe resulting mixture washed with saturated saline
3. 3
   Extractionextracted with ethyl acetate
4. 4
   OtherThe organic layer was separated
5. 5
   Dryingdried over anhydrous MgSO4
6. 6
   Concentrationconcentrated under a reduced pressure
7. 7
   OtherThe resulting residue was purified by flash chromatography

Procedure

1-Bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (120 mg, 0.32 mmol) obtained in Example 18 was dissolved in THF (10 mL), and benzylamine (102.87 mg, 0.11 mL, 0.93 mmol) and sodium iodide (9.60 mg, 0.06 mmol) were added thereto, followed by refluxing for 6 hrs. The resulting mixture washed with saturated saline and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 56 mg of the titled compound (yield: 44%).

Source