Water → 7-[(E)-2-(1-methyl-1H-imidazol-2-yl)-vinyl]-imidazo[1,2-a]pyridine
Reaction equation
C[C:2]([CH3:5])([O-])C.[K+].[N:7]1[CH:8]=[CH:9][N:10]2[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][C:11]=12.O>O1CCCC1>[CH3:11][N:7]1[CH:8]=[CH:9][N:10]=[C:2]1/[CH:5]=[CH:16]/[C:13]1[CH:14]=[CH:15][N:10]2[CH:9]=[CH:8][N:7]=[C:11]2[CH:12]=1Participants
Procedure
To a stirred solution of 2-triphenylphosphonium-1-methyl-1H-imidazole chloride (656 mg, 1.6 mmol, 1 equiv) in tetrahydrofuran (5 ml) at room temperature was added dropwise a solution of potassium tert-butoxide in tetrahydrofuran (1M, 3.3 ml, 3.3 mmol, 2 equiv). This brightly orange mixture was stirred thus for 2 hours and then a solution of imidazo[1,2-a]pyridine-7-carbaldehyde (245 mg, 1.7 mmol, 1 equiv) in tetrahydrofuran (8 ml) was added and the lightly coloured mixture was stirred at room temperature overnight. To the reaction was added water and the mixture was extracted with ethyl acetate. The organic liquors were washed with water and brine and then dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (0-20% methanol/ethyl acetate) furnishing 7-[(E)-2-(1-methyl-1H-imidazol-2-yl)-vinyl]-imidazo[1,2-a]pyridine (87 mg). MS:
Workup
- stirringthe lightly coloured mixture was stirred at room temperature overnight
- extractionthe mixture was extracted with ethyl acetate
- washThe organic liquors were washed with water and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography (0-20% methanol/ethyl acetate)
Sources & evidence
- ORD record
- ord-4ffd28b0a5994afebd3b581ec386280b
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796244B2
Reaction notes
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