Formaldehyde → 3-[({6-[4-Isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-pyridin-3-yl}-methyl-amino)-methyl]-benzoic acid methyl ester

Participants

Reaction Steps

To an ambient temperature solution of 6-[4-isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-pyridin-3-ylamine (100 mg, 0.246 mmol) in MeOH (3 mL) is added 3-formyl-benzoic acid methyl ester (40 mg, 0.246 mmol). The reaction mixture is stirred at room temperature for 10 min. Decaborane (12 mg, 0.0738 mmol) is added and the reaction mixture is stirred at room temperature. After 2 h, formaldehyde (2.0 mL, 37 wt % in water) is added and the reaction mixture is stirred at room temperature for 10 min. Decaborane (12 mg, 0.0738 mmol) is added and the reaction is stirred at room temperature. After 2 h, the reaction mixture is concentrated and the residue is chromatographed (SiO2 40 g, 0% to 20% EtOAc/Hex) to yield the title compound (97 mg, 69%). 1H NMR (400 MHz, DMSO) δ 7.91-7.88 (m, 1H), 7.81 (dt, 1H, J=4.6, 2.5 Hz), 7.63 (s, 1H), 7.59-7.50 (m, 4H), 7.48-7.41 (m, 3H), 6.39 (d, 1H, J=7.9 Hz), 5.13 (s, 2H), 4.00 (s, 2H), 3.82 (s, 3H), 3.03 (sept, 1H, J=6.6 Hz), 2.46 (s, 3H), 2.32 (s, 3H), 1.18 (d, 6H, J=6.6 Hz).

Provenance & Evidence