[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH:12](OC)O)[N:6]=[CH:5]2.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>C(Cl)Cl.CO.CC(O)=O>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[N:6]=[CH:5]2To a solution of 2-(5-iodo-1H-indazol-1-yl)-1-methoxyethanol (360 mg, 1.13 mmol) in CH2Cl2 (10.0 mL), MeOH (10.0 mL) and AcOH (4.0 mL) was added morpholine (295 mg, 3.39 mmol) and picoline-borane complex (120 mg, 1.13 mmol). The solution was stirred at ambient temperature for 1.5 h. The reaction mixture was concentrated, diluted with 1 N HCl (10.0 mL) and stirred at ambient temperature for 30 minutes. The mixture was made basic with 1N NaOH (10.0 mL) and extracted with EtOAc (3×50 mL). The organics were dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography (12 g ISCO column, eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 90% methylene chloride over 30 min at 20 mL/min) gave the title compound (164 mg, 41%) as an off-white powder. 1H NMR (300 MHz, CDCl3) 8.08 (d, J=1.0 1H), 7.90 (s, 1H), 7.7.62-7.56 (dd, J=8.8, 1.6 Hz, 1H), 7.23 (d, J=8.8 Hz, 1H), 4.47 (t, J=6.9 Hz, 2H), 3.64 (t, J=4.7 Hz, 4H), 2.85 (t, J=6.9, 2H), 2.48 (d, J=4.7 Hz, 4H).
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