HCID 178492258, compound → 5-methoxy-2-phenyl-1H-indole
Reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6](/[N:7]=[C:8](/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)\[CH3:9])=[CH:5][CH:4]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2].CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:16][CH:17]=1)[NH:7][C:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[CH:9]2Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
A 100 mL round-bottom flask equipped with a stirrer bar was charged with (E)-4-methoxy-N-(1-phenylethylidene)aniline (10 mmol, 2.25 g), Pd(OAc)2 (0.22 g, 1 mmol, 10 mol %) and Bu4NBr (6.45 g, 20 mmol, 2 equiv), followed by addition of DMSO (50 mL). The flask was quickly evacuated, closed under vacuum, and then refilled with oxygen using an oxygen balloon. The resulting mixture was stirred at 60° C. for 24 h. Upon cooling to room temperature, the reaction mixture was diluted with 25 mL of ethyl acetate, followed by filtration through a pad of silica gel. The filtrate was concentrated under vacuum, and the residue was purified on silica gel to afford the title compound as an off-white solid (1.87 g, 84%).
Workup
- customA 100 mL round-bottom flask equipped with a stirrer bar
- customThe flask was quickly evacuated
- customclosed under vacuum
- additionrefilled with oxygen using an oxygen balloon
- temperatureUpon cooling to room temperature
- additionthe reaction mixture was diluted with 25 mL of ethyl acetate
- filtrationfollowed by filtration through a pad of silica gel
- concentrationThe filtrate was concentrated under vacuum
- customthe residue was purified on silica gel
Sources & evidence
- ORD record
- ord-ef8657eaeca94bb2aab64a46062768ec
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09334275B2
Reaction notes
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