Dibenzyl-[2,4-difluoro-3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-amine (prepared as described in Example 22) (150 mg, 0.551 mmol) was dissolved in a 1:1:1 mixture of methanol, acetic acid and water (18 mL). Freshly distilled 2,5-difluorobenzaldehyde (0.180 mL, 1.653 mmol, 3 eq) was then added, followed by sodiumcyanoborohydride (2.424 mmol, 4.4 eq) and the mixture was stirred at room temperature for 5 hours. It was then poured into water, basified to pH 10 by addition of a saturated aqueous solution of Na2CO3 and extracted with ethyl acetate (3×30 mL). The combine dorganic layers were washed with brine, dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography on silica gel (DCM/MeOH 96:4) to give 124 mg (85%) of (2,5-difluoro-benzyl)-[2,4-difluoro-3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-amine a white solid.
