[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=O)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.CN([C:18]([O:22][N:23]1N=NC2C=CC=N[C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl.O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([N:23]([O:22][CH3:18])[CH3:24])=[O:14])[CH:10]=2)[N:5]=[CH:4][CH:3]=1To a mixture of 4-bromoquinoline-6-carboxylic acid (5 g), CH3ONH(CH3) hydrochloride salt (1.8 eq. 3.5 g), and HATU (1.15 eq. 8.67 g) in CH2Cl2 (100 mL) was slowly added triethylamine (4 eq. 11 mL) at 0° C. and the resulting reaction mixture was stirred at room temperature overnight. The reaction was diluted with CH2Cl2 and water. The combined organics were washed with water several times, concentrated and then purified by chromatography (60-70% EtOAc/hexanes) to yield 4-bromo-N-methoxy-N-methylquinoline-6-carboxamide as a white solid.
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