[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[N:6][C:7]=1[O:8][CH3:9].[CH2:14]1CCC(N=C=NC2CCCCC2)C[CH2:15]1.CCO.O>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:14]([O:12][C:11](=[O:13])[CH2:10][C:4]1[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([Br:1])[CH:3]=1)[CH3:15]To a solution of (5-bromo-6-methoxy-pyridin-3-yl)-acetic acid (Step AN2) (400 mg, 1.6 mmol) in CH2Cl2 (0.8 mL) was added DCC (18 mg, 0.09 mmol), DMAP (one spatula) and EtOH (4.88 mmol) and the mixture was stirred at rt for 15 h. H2O and EtOAc were added and the phases were separated. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (heptane/EtOAc, 85:15→0:100). ESI-MS: tR=1.05 min, [M+H]+ 274.1/276.1 (LC-MS 1).
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