Br[C:2]1[C:3](=[O:13])[N:4]([CH3:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:14]([O:18][C:19](=[O:28])[NH:20][CH2:21][C:22](N(OC)C)=[O:23])([CH3:17])([CH3:16])[CH3:15].C([Mg]Cl)(C)C>C1COCC1.ClCCl>[C:14]([O:18][C:19](=[O:28])[NH:20][CH2:21][C:22]([C:2]1[C:3](=[O:13])[N:4]([CH3:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:23])([CH3:17])([CH3:15])[CH3:16]To a 0.3 M solution of 3-bromo-1-methylquinolin-2(1 H)-one (1 equiv; prepared as described in Tetrahedron, 64 (26), 6030-6037; 2008) and tert-butyl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (1.2 eq) in dry THF, isopropylmagnesium chloride (3 eq) was added dropwise at room temperature. The mixture was stirred for 30 min at room temperature, diluted with dichloromethane, washed with sat. aq. NH4Cl dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, Pethroleum ether/EtOAc, from 7% to 60% EtOAc). The pooled fractions were concentraded under vacuum to the title compound. MS (ES) C17H20N2O4 requires: 316.35, found: 317. 1H-NMR (400 MHz, DMSO-d6) δ: 8.53 (1 H, s), 7.99 (1 H, d, J=7.2 Hz), 7.78 (1 H, t, J=6.8 Hz), 7.61 (1 H, d, J=8.4 Hz), 7.35 (1 H, t, J=7.2 Hz), 6.97 (1 H, bt, J=5.6 Hz), 4.45 (1 H, d, J=5.6 Hz), 3.70 (3 H, s), 1.39 (9 H, s).
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