[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([CH:18](O)[CH3:19])=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1.FC1C=C(B(O)O)C=CC=1.C(N(CC)CC)C.CS(Cl)(=O)=O.S([O-])(=O)(=O)C.CN(C)C=O.[N-:53]=[N+:54]=[N-:55].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:53]([CH:18]([C:9]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[CH3:19])=[N+:54]=[N-:55]To a mixture of 1-[8-(3-fluorophenyl)quinolin-7-yl]ethanol (0.160 g, 0.598 mmol) (prepared in analogy to Example 7 step 1-4, using (3-fluorophenyl)boronic acid instead of (2-fluorophenyl)boronic acid as starting material) in methylene chloride (4 mL) was added triethylamine (0.125 mL, 0.898 mmol), followed by methanesulfonyl chloride (0.0579 mL, 0.748 mmol). After stirring at room temperature for 30 minutes, the resultant mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The crude mesylate was dissolved in N,N-dimethylformamide (2 mL, 20 mmol) and treated with sodium azide (0.194 g, 2.99 mmol) at room temperature overnight. After diluted with ethyl acetate, the mixture was washed with water and brine and then dried over magnesium sulfate and evaporated to dryness. The crude product was used in the next step. LCMS calculated for C17H14FN4(M+H)+: m/z=293.1; found: 293.0.
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