Water → 7-[(Pyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazole
Reaction equation
I[C:2]1[N:3]=[CH:4][N:5]2[CH:9]=[CH:8][S:7][C:6]=12.C[Mg]Br.C1COCC1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=[O:25])[CH:19]=1.O>C1COCC1>[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([OH:25])[C:2]2[N:3]=[CH:4][N:5]3[CH:9]=[CH:8][S:7][C:6]=23)[CH:19]=1Participants
Procedure
A solution of 2.50 g of 7-iodoimidazo[5,1-b]thiazole in 50 ml of dry THF was cooled in ice, and 11.3 ml of a 0.93 M methylmagnesium bromide/THF solution was added to the cooled solution under an argon atmosphere. The mixture was stirred at that temperature for 20 min. Pyridine-3-aldehyde (1.04 ml) was then added thereto, and the mixture was stirred at that temperature for 40 min and then at room temperature for 4 hr. Water was added to the reaction solution, and the mixture was extracted five times with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1) to give 1.925 g of 7-[(pyridin-3-yl)hydroxymethyl]imidazo[5,1-b]thiazole.
Workup
- stirringthe mixture was stirred at that temperature for 40 min
- waitat room temperature for 4 hr
- extractionthe mixture was extracted five times with dichloromethane
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationwas then concentrated under the reduced pressure
- customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=20:1)
Sources & evidence
- ORD record
- ord-82ca0b1c99f7439c9cca97c0487bd524
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06908913B2
Reaction notes
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