[N:1]1([C:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[C:12]([C:19](=[O:21])[CH3:20])[CH:13]=[CH:14][CH:15]=3)[N:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Si](OS(C(F)(F)F)(=O)=O)(C(C)(C)C)(C)C.O.C1C(=O)N([Br:45])C(=O)C1>C(Cl)Cl.C1COCC1>[Br:45][CH2:20][C:19]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[N:10]=[C:9]([C:7]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:8])[CH:18]=[CH:17]2)=[O:21]
To a solution of 1-(2-(morpholine-4-carbonyl)quinolin-8-yl)ethanone (0.438 g, 1.54 mmol) in DCM (5 mL) at 0° C. was added TEA (0.28 ml, 2.00 mmol) followed by TBSOTf (0.39 mL, 1.70 mmol). The resulting mixture was stirred at 0° C. for 50 min. The mixture was then partitioned between saturated NaHCO3 and DCM. The organic layer was separated, and the aq. layer was extracted with DCM (3×). The combined organic layers were then dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give a brown oil. The resulting oil was taken up in THF (8 mL) and treated with water (0.44 mL, 24.7 mmol) and NBS (288 mg, 1.62 mmol). The resulting solution was stirred at RT for 20 min. The reaction mixture was then partitioned between water and Et2O, and the organic layer was separated and sequentially washed with saturated NaHCO3, water, and brine, then dried over MgSO4, filtered, and concentrated in vacuo to give a 2-bromo-1-(2-(morpholine-4-carbonyl)quinolin-8-yl)ethanone as a greenish-brown solid. This material was used in the subsequent step without purification, assuming the theoretical yield: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.66 (d, J=8.6 Hz, 1H), 8.29 (dd, J=8.1, 1.3 Hz, 1H), 8.11 (dd, J=7.2, 1.4 Hz, 1H), 7.77-7.85 (m, 2H), 3.72 (s, 4H), 3.61-3.62 (m, 2H), 3.57-3.59 (m, 2H), 3.51-3.57 (m, 2H). m/z (ESI, +ve ion) 363.0/365.0 (M+H)+.
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