Water → HCID 23362844, compound
Reaction equation
O[CH2:2][CH2:3][CH2:4][S:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1.[H-].[Na+].[CH3:17][C:18]1[IH][CH:20]=[CH:21][CH:22]=1.O.[O:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>>[C:25]1([CH2:26][CH2:27][CH2:28][O:24][CH2:2][CH2:3][CH2:4][S:5][C:6]2[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)[CH:20]=[CH:21][CH:22]=[CH:18][CH:17]=1Participants
Procedure
To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.070 g, 5.137 mmoles) in tetrahydrofuran (30 ml) was added 60% sodium hydride in oil (0.25 g, 6.2 moles) with stirring under ice-cooling and the mixture was stirred under ice-cooling for 30 minutes. To the reaction mixture was added methyl iodie (1.53 g, 7.71 mmoles), followed by stirring at room temperature overnight. The reaction mixture was poured into water, which was extracted with methylene chloride (30 ml×3). The methylene chloride layers were combined and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent:ethyl acetate) to obtain 0.987 g of the desired compound (58.9%, light brown oily product).
Workup
- temperaturecooling
- stirringthe mixture was stirred under ice-
- temperaturecooling for 30 minutes
- stirringby stirring at room temperature overnight
- extractionwas extracted with methylene chloride (30 ml×3)
- dry with materialdried over anhydrous magnesium sulfate
- distillationAfter the solvent was distilled off
- customthe residue was purified by column chromatography (eluent:ethyl acetate)
Sources & evidence
- ORD record
- ord-04761f3c1d6144c9bcaba5183d251d1c
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05587383
Reaction notes
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