Cesium carbonate → 6-(2-Chloropyridin-4-yloxy)-2-(methylthio)benzo[d]thiazole
Reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:19][C:20]1[CH:25]=[C:24](F)[CH:23]=[CH:22][N:21]=1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[Cl:19][C:20]1[CH:25]=[C:24]([O:12][C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:3]([S:2][CH3:1])[S:4][C:5]=3[CH:11]=2)[CH:23]=[CH:22][N:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
To the mixture of 2-(methylthio)benzo[d]thiazol-6-ol (1 g, 5.08 mmol) and cesium carbonate (4.55 g, 14 mmol) in 15 ml of NMP was added 2-chloro-4-fluoropyridine (1.32 mg, 10 mmol). The reaction mixture was stirred at 55° C. for overnight. The reaction mixture was poured into 80 ml of aq. saturated NaHCO3 and extracted with ethyl acetate (2×150 ml). The combined organic layers were washed with aq. 0.1M NaHSO4 (60 ml), water (2×60 ml) and brine (60 ml), then dried over MgSO4, filtered and evaporated in vacuo to give 6-(2-chloropyridin-4-yloxy)-2-(methylthio)benzo[d]thiazole (1.72 g) as brown oil that carried on to next step without purification. ES/MS m/z 308.9 (MH+).
Workup
- extractionextracted with ethyl acetate (2×150 ml)
- washThe combined organic layers were washed with aq. 0.1M NaHSO4 (60 ml), water (2×60 ml) and brine (60 ml)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-5d56145f6237439b8d0eedd991481866
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173689B2
Reaction notes
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