COC(C1C=C(O)N(C2C=CC=CC=2F)N=1)=O.C(=O)([O-])[O-].[Cs+].[Cs+].BrCC1C=CC=CC=1C#N.C[O:35][C:36]([C:38]1[CH:42]=[C:41]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]#[N:52])[N:40]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[F:59])[N:39]=1)=[O:37].[OH-].[Li+]>CN(C=O)C.C1COCC1.O>[C:51]([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=1[CH2:44][O:43][C:41]1[N:40]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[F:59])[N:39]=[C:38]([C:36]([OH:37])=[O:35])[CH:42]=1)#[N:52]1-(2-Fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid methyl ester (200 mg, 0.847 mmol) were dissolved in 5 ml of DMF and cesium carbonate (552 mg, 1.7 mmol) and 2-bromomethyl-benzonitrile (166 mg, 0.85 mmol) were added. The mixture was stirred for 5 h at 60° C., filtrated and the solvent was removed in vacuo. The obtained residue of crude 5-(2-cyano-benzyloxy)-1-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid methyl ester (235 mg, 79%) was dissolved in a mixture of THF, MOH and water (3 ml each), lithium hydroxide (64.1 mg, 2.7 mmol) was added, and the mixture was stirred overnight at room temperature. After evaporation of the solvent the residue was subjected to column chromatography (silica gel, DCM/MOH 9:1) to give 195 mg (86%) of the title compound.
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