Triethylamine → Imidazo(1,2-a)pyridine
Reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.C(N(CC)CC)C.CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC>O1CCOCC1>[N:10]1[CH:9]=[CH:8][N:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=12Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
The obtained 2-[4′-(2″-hydroxyethoxy)]phenyl]-6-iodoimidazo[1,2-a]pyridine was dissolved in dioxane, and triethylamine is added thereto. Then, bis(tributyltin) and a catalytic amount of tetrakis-triphenylphosphine palladium are added thereto. This reaction mixture is heated at about 90° C. and reacted for about 24 hours, and then a solvent is distilled off and chromatographic purification is performed to obtain 6-tributylstannyl-2-[4′-(2″-hydroxyethoxy)]phenyl]imidazo[1,2-a]pyridine as the target compound (FIG. 2-2, Step 1). The amount of bis(tributyltin) to be used in this instance may be an amount satisfying a condition where it is excessive relative to the reaction substrate, specifically, it is about 1.5 times in molar ratio relative to the reaction substrate 2-[4′-(2″-hydroxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine.
Workup
- customreacted for about 24 hours
- distillationa solvent is distilled off
- customchromatographic purification
Sources & evidence
- ORD record
- ord-b63cc3ca6ea240f6a7ccd026ba0fb8f7
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08506930B2
Reaction notes
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