4-Chlorophenol → Methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9]C(C)([O-])C.[K+].Cl[C:16]1[CH:17]=[N:18][CH:19]=[C:20](Cl)[C:21]=1[CH:22]=O.C[CH:26]([SH:30])[C:27]([O-:29])=[O:28].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:20]2[CH:19]=[N:18][CH:17]=[C:16]3[S:30][C:26]([C:27]([O:29][CH3:9])=[O:28])=[CH:22][C:21]=23)=[CH:4][CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 4-chlorophenol (2.63 g, 20.5 mmol) in THF (20 mL) at 0° C. was treated dropwise with a solution of potassium tert-butoxide (1.0 M solution in THF, 20.4 mL, 20.5 mmol), stirred at 25° C. for 1 hour, cooled to 0° C., treated with a solution of Example 17A (3.54 g, 20.23 mmol) in THF (40 mL), warmed at 60° C. for 0.5 hours, cooled to 0° C., treated with methylthioglycolate (1.989 mL, 22.25 mmol) and Cs2CO3 (6.59 g, 20.23 mmol), warmed at 60° C. for 0.25 hours, cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate, washed sequentially with water and brine, dried (MgSO4), filtered, and concentrated. Purification of the residue by flash chromatography on silica gel with 4% acetone/hexane provided the title compound.
Workup
- temperaturecooled to 0° C.
- temperaturewarmed at 60° C. for 0.5 hours
- temperaturecooled to 0° C.
- temperaturewarmed at 60° C. for 0.25 hours
- temperaturecooled to room temperature
- filtrationfiltered
- additionThe filtrate was diluted with ethyl acetate
- washwashed sequentially with water and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customPurification of the residue by flash chromatography on silica gel with 4% acetone/hexane
Sources & evidence
- ORD record
- ord-4aa5b9a27a5f4f1db42c118260a2621f
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06232320B1
Reaction notes
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