Sodium Carbonate → (E)-4-(Hex-3-en-3-yl)-3-methyl-1H-imidazo[4,5-c]pyridin-2(3H)-one
Reaction equation
Br[C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:19][CH2:20]/[C:21](/B1OC2C=CC=CC=2O1)=[CH:22]\[CH2:23][CH3:24]>C1(C)C=CC=CC=1>[CH3:19][CH2:20]/[C:21](/[C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1)=[CH:22]\[CH2:23][CH3:24]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 0.68 g (3.0 mmol) of 4-bromo-3-methyl-1H-imidazo[4,5-c]pyridin-2(3H)-one and 0.17 g (0.20 mmol) of PdCl2dppf-dichloromethane complex was dissolved in 12 mL of toluene and treated with 3.8 mL (7.7 mmol) of 2N sodium carbonate and 0.72 g (3.6 mmol) of (Z)-2-(hex-3-en-3-yl)benzo[d][1,3,2]dioxaborole. The resulting mixture was heated to 90° C. for 5 h, partitioned between water and ethyl acetate, filtered to remove fine precipitates and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The brown oil thus obtained was purified by flash chromatography eluting with a 25% methanol/dichloromethane mixture to give 0.40 g (58%) of the title compound as a cream colored solid.
Workup
- custompartitioned between water and ethyl acetate
- filtrationfiltered
- customto remove fine
- customprecipitates
- extractionextracted with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe brown oil thus obtained
- customwas purified by flash chromatography
- washeluting with a 25% methanol/dichloromethane mixture
Sources & evidence
- ORD record
- ord-d20a50eece114294bf539eb6801bde7f
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163935B2
Reaction notes
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