CS(Cl)(=O)=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]([CH3:21])=[C:16]([CH2:18][CH2:19]O)[N:17]=2)=[CH:9][CH:8]=1.C([N:24]([CH2:27][CH3:28])[CH2:25]C)C.BrC1C=CC(C2OC(C)=C(CCOS(C)(=O)=O)N=2)=CC=1.N1CCC1>ClCCl.O1CCCC1>[N:24]1([CH2:19][CH2:18][C:16]2[N:17]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([Br:6])=[CH:8][CH:9]=3)[O:14][C:15]=2[CH3:21])[CH2:25][CH2:28][CH2:27]1Add methanesulfonyl chloride (0.745 g, 6.50 mmol) to a cool (0° C.) solution of 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol (1.4 g, 5.0 mmol) and triethylamine (1.26 g, 12.5 mmol) in dichloromethane (20 mL). Warm to room temperature and stir for 1 hour. Remove solvents, transfer crude of methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester residue to a sealed tube, add tetrahydrofuran (30 mL), azetidine (2.0 g, 35.5 mmol), and heat at 60° C. overnight. Wash the crude organic material with 1N HCl. Separate layers and add 5N NaOH to the aqueous layer until it is basic. Extract the aqueous layer with diethyl ether (2×50 mL), dry the organic extracts over Na2SO4, filter, and concentrate. Purify on silica gel eluting with 10% ammoniated methanol in dichloromethane to give 4-(2-azetidin-1-yl-ethyl)-2-(4-bromo-phenyl)-5-methyl-oxazole (1.22 g, 72%): mass spectrum (m/e): 323 (M+1).
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