Ethyl Acetate → 2-(Methylthio)-6-(quinolin-4-yloxy)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[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][CH:21]=1.C(OCC)(=O)C>CN1C(=O)CCC1>[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([O:12][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=[CH:22][CH:21]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1Participants
Procedure
To the reaction mixture of 2-(methylthio)benzo[d]thiazol-6-ol (750 mg, 3.79 mmol) in 10 ml of NMP was added Cesium Carbonate (3.2 g, 9.5 mmol) and stirred at RT for 3 minutes. To this mixture was added 4-chloroquinoline (682 mg, 4.17 mmol). The reaction mixture was stirred at 110° C. for 24 hours. The reaction was worked up by adding 250 ml ethyl acetate and washed with 75 ml of saturated NaHCO3, 2×60 ml water, 1×50 ml saturated NaCl, dried with sodium sulfate, filtered and concentrated in vacuo. The resulting solid residue was purified by silica gel column chromatography, eluted with (40% EtOAc: 60% Hexanes) and concentrated in vacuo to give 2-(methylthio)-6-(quinolin-4-yloxy)benzo[d]thiazole as solid (980 mg). ES/MS m/z 325.1 (MH+).
Workup
- stirringThe reaction mixture was stirred at 110° C. for 24 hours
- washwashed with 75 ml of saturated NaHCO3, 2×60 ml water, 1×50 ml saturated NaCl
- dry with materialdried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting solid residue was purified by silica gel column chromatography
- washeluted with (40% EtOAc: 60% Hexanes)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3fe52fad931146fa9dcd367208302ac6
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173689B2
Reaction notes
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