[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](=[O:14])[N:12]3[CH:15]=[CH:16][S:17][C:11]3=[N:10][C:9]=2[CH3:18])=[CH:4][CH:3]=1.[CH2:19](Br)[CH3:20].[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13](=[O:14])[N:12]3[CH:15]=[CH:16][S:17][C:11]3=[N:10][C:9]=2[CH3:18])=[CH:6][CH:7]=1)[CH3:20]To a solution of Step 1 intermediate (250 mg, 0.967 mmol) in DMF (4 ml) was added ethyl bromide (0.147 g, 1.355 mmol) and NaH (0.053 g, 1.355 mmol) and heated to 80° C. for 15.0 h. After completion of the reaction, the mixture was diluted with ethyl acetate, washed with water, brine, dried over anhydrous Na2SO4 to afford 300 mg of the desired compound as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.34 (t, J=6.6 Hz, 3H), 2.17 (s, 3H), 4.05 (q, J=6.6 Hz, 2H), 6.93-6.96 (m, 2H), 7.17-7.20 (m, 2H), 7.50 (d, J=4.5 Hz, 1H), 7.98 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 311.28 (M+H)+.
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