Sulfonium → 3-Bromo-4-(oxetan-2-YL)pyridine
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[CH3:1]C(C)([O-])C.[K+].[SH3+].[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:17][O:16]1>CC(O)(C)C.CS(C)=O>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:17][CH2:1][O:16]1[CH3:1]C(C)([O-])C.[K+].[SH3+].[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:17][O:16]1>CC(O)(C)C.CS(C)=O>[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:17][CH2:1][O:16]1potassium tert-butoxide (561 mg, 5 mmol) was added to a solution of sulfonium salt (1100 mg, 5 mmol) in t-BuOH (20 mL) at room temperature. After 15 min, a solution of 3-Bromo-4-oxiranyl-pyridine (200 mg, obtained above) in DMSO (10 mL) was added dropwise at 50° C. The resulting mixture was stirred at 50° C. for 15 h. The reaction mixture was quenched with brine, and the resulting mixture was extracted with ethyl acetate twice. The combined extracts were dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by flash column and afforded the title compound (96 mg). ESI-MS m/z: 216.1 [M+1]+, Retention time 1.01 min; 1HNMR (CDCl3, 400.342 MHz) δ ppm 2.50-2.59 (m, 1H), 3.31-3.39 (m, 1H), 4.65-4.70 (m, 1H), 4.87-4.92 (m, 1H), 5.91 (t, J=8 Hz, 1H), 7.95 (d, J=8 Hz, 1H), 8.68 (d, J=8 Hz, 1H), 8.73 (s, 1H).
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