Sodium Iodide → 1-benzylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7](Br)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[I-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH:31][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]Participants
5
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%).
Workup
- temperatureby refluxing for 6 hrs
- washThe resulting mixture washed with saturated saline
- extractionextracted with ethyl acetate
- customThe organic layer was separated
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated under a reduced pressure
- customThe resulting residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-850aa1a6feec4aa5a9012bc8bff7fe18
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745439B2
Reaction notes
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