Methyl imidazo(1,2-a)pyridine-6-carboxylate → 5,6,7,8-Tetrahydro-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester
Reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:6][C:5]=12>[Pd].C(O)(=O)C>[N:1]1[CH:2]=[CH:3][N:4]2[CH2:9][CH:8]([C:10]([O:12][CH3:13])=[O:11])[CH2:7][CH2:6][C:5]=12Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a 50 ml pressure bottle were placed methyl imidazo[1,2-a]pyridine-6-carboxylate (0.26 g), acetic acid (10 mL), and wet 5% palladium on carbon (0.052 g). The reaction mixture was stirred for 16 hours at 30 psi and 50° C. The solid was filtered off, and the filtrate was concentrated. The residue was dissolved in ethyl acetate. It was then washed with saturated sodium bicarbonate, brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel to give the title compound.
Workup
- filtrationThe solid was filtered off
- concentrationthe filtrate was concentrated
- dissolutionThe residue was dissolved in ethyl acetate
- washIt was then washed with saturated sodium bicarbonate, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash column chromatography on silica gel
Sources & evidence
- ORD record
- ord-91d3ffbd74fe4215aeff64d53e27ac24
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073855B2
Reaction notes
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