CO[C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1.Br[C:13]1[CH:14]=[CH:15][C:16](C(N)=O)=[N:17][CH:18]=1.[CH3:22][O:23]C1C=CC2N=C(C3C=CC(C(F)(F)F)=CN=3)SC=2C=1.[CH3:43][N:44](C=O)C>[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:22][O:23][C:11]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:13]3[CH:14]=[CH:15][C:16]([NH:44][CH3:43])=[N:17][CH:18]=3)=[N:7][C:6]=2[CH:10]=16-Methoxy-1,3-benzothiazole (0.100 g, 0.61 mmol) and 5-bromopyridine-2-carboxamide (0.146 g, 0.73 mmol) were reacted according to the procedure used for the preparation of 6-methoxy-2-[5-(trifluoromethyl)pyridin-2-yl]-1,3-benzothiazole, with the following exceptions: 10 mol % bis(tri-t-butylphosphine) palladium (0) was used and the amount of DMF was reduced (3 mL). The reaction mixture was concentrated and flash chromatography of the residue gave the title compound (10 mg) as an off-white solid. 1H NMR δ 9.25 (dd, 1H) 8.56 (dd, 1H) 8.23 (br s, 1H) 8.19 (dd, 1H) 8.04 (d, 1H) 7.81 (d, 1H) 7.78 (br s, 1H) 7.20 (dd, 1H) 3.88 (s, 3H); MS m/z (M+H) 286.
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