Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[C:18]([C:21]1[S:25][C:24](B(O)O)=[CH:23][CH:22]=1)(=[O:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>C(N(CC)CC)C>[CH3:17][O:16][C:14](=[O:15])[CH2:13][CH2:12][NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:24]3[S:25][C:21]([C:18](=[O:20])[CH3:19])=[CH:22][CH:23]=3)=[CH:3][N:4]=2)[N:7]=1The methyl 3-((3-bromoimidazo[1,2-b]pyridazin-6-yl)amino)propanoate was then subjected to Suzuki coupling reaction with (5-acetyl-thiophen-2-yl)boronic acid as described in example 5.6.19. However for this reaction, triethylamine was used as the base in place of the regular base (K2CO3). The desired product was obtained in 79% yield. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.62-2.65 (m, 3H) 2.88 (t, J=5.94 Hz, 2H) 3.77 (s, 3H) 3.88 (t, J=5.68 Hz, 2H) 7.06 (d, J=9.85 Hz, 1H) 7.70 (d, J=4.04 Hz, 1H) 7.77 (d, J=4.04 Hz, 1H) 8.15 (s, 1H) 8.33 (d, J=9.85 Hz, 1H); LRMS (ESI) m/e 345.0 [(M+H)+, calcd for C16H16N4O3S 344.0].
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