Potassium Carbonate → HCID 67046930, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)[CH3:2].[CH3:13][C:14]1[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:20][C:19]2[C:14]([CH3:13])=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A reaction tube containing a magnetic stirrer bar was charged with ethyl-4-fluorobenzoate (1 mmol), 2-methyl-3-pyridol (1.0 mmol), potassium carbonate (1.08 mmol) and DMF (2 ml). The reaction tube was then sealed and heated by microwave irradiation (100 W, 4 mins) to 150° C. and held at that temperature for 80 mins. The solution was filtered to remove the insoluble potassium carbonate and then concentrated in vacuo. The residue was purified by preparative HPLC and freeze dried to give 4-(2-Methyl-pyridin-3-yloxy)-benzoic acid ethyl ester as a white solid which was hydrolysed by 6N aqueous HCl solution heated by microwave irradiation (200 W) for 3 mins at 150° C. The solution was freeze dried to give to 63 mg of hydrochloride salt of the title compound as a white powder m/z=229 in MS ES+, which was characterised by HPLC and MS.
Workup
- additionA reaction tube containing a magnetic stirrer bar
- customThe reaction tube was then sealed
- filtrationThe solution was filtered
- customto remove the insoluble potassium carbonate
- concentrationconcentrated in vacuo
- customThe residue was purified by preparative HPLC
- customfreeze dried
Sources & evidence
- ORD record
- ord-58c706afc41049eea2e30517ee207653
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915300B2
Reaction notes
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