C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]Br)=[CH:11][C:10]=1[F:18])C1C=CC=CC=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:18][C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:13]=[CH:14][C:9]=1[OH:8]To a solution of 1-benzyloxy-4-(2-bromo-ethyl)-2-fluoro-benzene (1.0 g, 3.2 mmol) and morpholine (278 mg, 3.2 mmol) in DMF (5 mL), was K2CO3 (432 mg, 3.2 mmol) added. The reaction mixture was heated to 60° C. and maintained for 6 hours. The reaction was cooled to room temperature and poured into H2O (50 mL). The organic compound was extracted with ethyl acetate (50 mL) and dried over MgSO4. The ethyl acetate layer was concentrated under vacuum and dissolved in methanol (50 mL). The solution was treated with Pd/C (20 mg) and stirred under H2 (1 atm) for 3 hours. The solid material was filtrated off and the filtrate was concentrated under vacuum to afford the desired compound (790 mg, 93%) as a white oil. The crude compound was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.33-7.45 (m, 5H), 7.09-7.15 (m, 2H), 6.97-7.01 (m, 1H), 5.13 (s, 2H), 3.56 (m, 4H), 2.64-2.68 (m, 2H), 2.44-2.50 (m, 2H), 2.39 (b, 2H). LCMS 310.5 [MH+].
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