Reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=O.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[SH:21][CH2:22][C:23]([O:25][CH3:26])=[O:24]>O>[S:21]1[C:2]2=[CH:3][N:4]=[CH:5][CH:6]=[C:7]2[CH:8]=[C:22]1[C:23]([O:25][CH3:26])=[O:24]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a 50-mL round-bottom flask was added 3-fluoro-4-pyridinecarboxaldehyde (0.8 mL, 8.02 mmol) and N,N-dimethylformamide (14 mL) and the solution was cooled to 0° C. To this solution was added potassium carbonate (1.22 g, 8.828 mmol) and methyl 2-mercaptoacetate (0.754 mL, 8.427 mmol). The solution turned to a clear yellow solution after stirring for 10 min. After 30 min at 0° C., the reaction was warmed to room temperature and stirred over the weekend by which time a solid precipitate was formed. Water was added provide a homogeneous solution, which was cooled to 0° C., the solid was collected via vacuum filtration, and washed with cold water until clear and colorless affording methyl thieno[2,3-c]pyridine-2-carboxylate (1.55 g, 82%) as a white solid. LCMS: (FA) ES+ 194; 1H NMR (d6-DMSO, 300 MHz) δ9.37 (s, 1 H), 8.56 (d, J=5.4 Hz, 1 H), 8.26 (d, J=0.6 Hz, 1 H), 7.97 (dd, J=5.4 Hz, 1.2 Hz, 1 H), 3.92 (s, 3 H).
Workup
- waitAfter 30 min at 0° C.
- temperaturethe reaction was warmed to room temperature
- stirringstirred over the weekend by which time a solid precipitate
- customwas formed
- customprovide a homogeneous solution, which
- temperaturewas cooled to 0° C.
- filtrationthe solid was collected via vacuum filtration
- washwashed with cold water until clear and
Sources & evidence
- ORD record
- ord-5a840f9ea0034f61a9ec6848f2418dfb
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08624040B2
Linked notes
Loading…