2-(pyridin-3-yl)-1H-indole → 3-[p-(2-Ethoxycarbonylpropen-1-yl)benzyl]-2-(3-pyridyl)indole
Reaction equation
C([Mg]Br)C.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:6]=1.Cl[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[C:29]([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:24][CH:23]=1>O1CCCC1>[CH2:33]([O:32][C:30]([C:29]([CH3:35])=[CH:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:7]2[CH:6]=[N:5][CH:10]=[CH:9][CH:8]=2)=[CH:23][CH:24]=1)=[O:31])[CH3:34]Participants
Procedure
To 6.0 ml of a 2M solution of ethylmagnesium bromide in tetrahydrofuran under nitrogen at 0° is added dropwise over 20 minutes a solution of 2-(3-pyridyl)indole (1.9 g) in 12 ml of tetrahydrofuran. After complete addition the mixture is stirred at 0° for 0.5 hour and is then treated dropwise with a solution of 2.39 g of ethyl 3-(p-chloromethylphenyl)-2-methylacrylate in 5 ml of tetrahydrofuran. The resulting mixture is stirred at 0° for 1 hour, then at room temperature for 1 hour, and poured in 100 ml of ice-water. The resulting mixture is extracted with ether (2×50 ml) and the organic layer is washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 3-[p-(2-ethoxycarbonylpropen-1-yl)benzyl]-2-(3-pyridyl)indole.
Workup
- additionAfter complete addition the mixture
- stirringThe resulting mixture is stirred at 0° for 1 hour
- waitat room temperature for 1 hour
- extractionThe resulting mixture is extracted with ether (2×50 ml)
- washthe organic layer is washed with 100 ml of brine
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-e66166faa41c4101b91b7dab6c0acf47
- Source dataset
- uspto-grants-1985_04
- Patent number
- US04511573
Reaction notes
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