Water → 3-[4-(3-cyano-1-ethyl-5-methyl-2-pyrrolyl)benzyl]-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine
Reaction equation
[CH2:1]([S:3][C:4]1[NH:13][C:7]2=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]2[N:5]=1)[CH3:2].[H-].[Na+].[CH2:16]([N:18]1[C:22]([CH3:23])=[CH:21][CH2:20][C:19]1([C:26]1[CH:31]=[CH:30][C:29]([CH2:32]OS(C)(=O)=O)=[CH:28][CH:27]=1)C#N)[CH3:17].O.[CH3:39][N:40](C)C=O>>[C:39]([C:20]1[CH:21]=[C:22]([CH3:23])[N:18]([CH2:16][CH3:17])[C:19]=1[C:26]1[CH:27]=[CH:28][C:29]([CH2:32][N:13]2[C:7]3=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]3[N:5]=[C:4]2[S:3][CH2:1][CH3:2])=[CH:30][CH:31]=1)#[N:40]Participants
Reactant 5
Product 1
Procedure
To a solution of 2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine (3.00 g) in dimethylformamide (30 ml) was added sodium hydride (627 mg) portionwise at room temperature under nitrogen atmosphere. The mixture was stirred at room temperature for an hour. To the mixture was added a solution of 1-ethyl-2-(4-methanesulfonyloxymethyl phenyl)-5-methylpyrrole-2-carbonitrile (4.94 g) in dimethylformamide (50 ml). The reaction mixture was stirred at room temperature for 3 hours. Water was added therein, and extracted twice with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate, and concentrated. The residue was purified by flash column chromatography eluted by n-hexane/ethyl acetate (1/1) to give 3-[4-(3-cyano-1-ethyl-5-methyl-2-pyrrolyl)benzyl]-2-ethylthio-7-methyl-3H-imidazo[4,5-b]pyridine (1.52 g) as colorless oil.
Workup
- stirringThe reaction mixture was stirred at room temperature for 3 hours
- extractionextracted twice with ethyl acetate
- washThe extracts were washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by flash column chromatography
- washeluted by n-hexane/ethyl acetate (1/1)
Sources & evidence
- ORD record
- ord-e0a384cb3fad4317b991d049978b9923
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05354759
Reaction notes
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