[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:24])[C:6]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][C:16]=2[F:23])=[N:9][N:10]([CH3:14])[C:11]=1[C:12]#[N:13].S(C)C>C(Cl)Cl.B(F)(F)F>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:24])[C:6]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[F:23])=[N:9][N:10]([CH3:14])[C:11]=1[C:12]#[N:13]4-(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile (17 mg, 0.05 mmol) was dissolved in dry DCM (2 mL) and BF3.Me2S (1 M solution in DCM, 0.3 mL, 0.3 mmol) was added and the mixture was stirred at room temperature over night. The mixture was concentrated and MeOH was added to quench the reaction The crude product was purified on silica gel to give -(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile (7.0 mg, 43%).
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