[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][C:14]#[N:15])[S:11][CH:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][C:24]([O:27][CH2:28][CH2:29]Cl)([CH3:26])[CH3:25]>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:13]3([C:14]#[N:15])[CH2:29][CH2:28][O:27][C:24]([CH3:26])([CH3:25])[CH2:23]3)[S:11][CH:12]=2)=[CH:6][CH:7]=1
2-(4-(4-Fluorophenyl)thiazol-2-yl)acetonitrile (325 mg, 1.5 mmol), potassium carbonate (617 mg, 4.47 mmol), and 1-chloro-2-(2-chloroethoxy)-2-methylpropane (254 mg, 1.5 mmol) in DMF (5 mL) were microwaved at 160° C. for 5 min then 20 min. A second addition of potassium carbonate and 1-chloro-2-(2-chloroethoxy)-2-methylpropane was made and then the reaction was microwaved again for 30 min two times. The reaction was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and purified on silica using a gradient of 0-30% ethyl acetate/hexanes to afford 4-(4-(4-Fluorophenyl)thiazol-2-yl)-2,2-dimethyltetrahydro-2H-pyran-4-carbonitrile (228 mg, 48% yield). MS (ESI) m/z: Calculated for C17H17FN2OS: 316.10. found: 317.1 (M+H)+.
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