N,N,N',N'-Tetramethylethylenediamine → 5-(5-Cyanopentyl)-imidazo[1,5-a]pyridine
Reaction equation
[CH3:1][C:2]1[N:7]2[CH:8]=[N:9][CH:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C[N:12](C)[CH2:13][CH2:14]N(C)C.[CH2:19]([Li])[CH2:20][CH2:21]C.CCCCCC>O1CCCC1>[C:13]([CH2:14][CH2:19][CH2:20][CH2:21][CH2:1][C:2]1[N:7]2[CH:8]=[N:9][CH:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1)#[N:12]Participants
Procedure
A solution of 5-methylimidazo[1,5-a]pyridine (4.0 g) and tetramethylethylene diamine (4.9 g) in 100 ml of tetrahydrofuran is cooled to 0° under nitrogen and 26.5 ml of 1.6N n-butyllithium is hexane is added dropwise maintaining the temperature below 2°. After 30 minutes this solution is transferred under nitrogen over 45 minutes to an ice-cold solution of 5-bromovalerontrile (4.86 g) in 80 ml of tetrahydrofuran. After 15 minutes the solvent is evaporated and the residue is partitioned between water and ethyl acetate. The organic phase is reextracted with 2N hydrochloric acid (3×15 ml). Basification of the aqueous phase to pH=10 with 50% sodium hydroxide, extraction with ethyl acetate (2×75 ml), drying over magnesium sulfate, evaporation and chromatography (SiO2, ethyl acetate) yields 5-(5-cyanopentyl)-imidazo[1,5-a]pyridine.
Workup
- additionis added dropwise
- temperaturemaintaining the temperature below 2°
- customAfter 15 minutes the solvent is evaporated
- customthe residue is partitioned between water and ethyl acetate
- extractionBasification of the aqueous phase to pH=10 with 50% sodium hydroxide, extraction with ethyl acetate (2×75 ml)
- dry with materialdrying over magnesium sulfate, evaporation and chromatography (SiO2, ethyl acetate)
Sources & evidence
- ORD record
- ord-e3046ee1ce6d42468a171061cfba3f9f
- Source dataset
- uspto-grants-1984_09
- Patent number
- US04470986
Reaction notes
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