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 taken up 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 using 10-100% ethyl acetate in hexanes to provide the title compound.
Workup
- filtrationThe solid was filtered off
- concentrationthe filtrate was concentrated
- 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 using 10-100% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-ae7985a0380b48c1bc3f8bf595d39af6
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174982B2
Reaction notes
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