1-[5-(4-Methyl-pyrazol-1-yl)-2-nitro-phenyl]-piperidine → 4-(4-Methyl-pyrazol-1-yl)-2-piperidin-1-yl-phenylamine

Participants

Reaction Steps

1-[5-(4-Methyl-pyrazol-1-yl)-2-nitro-phenyl]-piperidine (110 mg, 0.38 mmol, as prepared in the previous step) was allowed to react with TiCl3 (2.3 mL, 3.8 mmol) in 3 mL of THF. The reaction was quenched with satd aq NaHCO3 (15 mL) and poured into 25 mL of EtOAc. The organic layer was separated, washed with water (2×25 mL), dried (Na2SO4), and concentrated in vacuo to afford 94 mg (95%) of 4-(4-methyl-pyrazol-1-yl)-2-piperidin-1-yl-phenylamine, which was allowed to react in a similar manner to Example 4, step (c), with 5-cyano-furan-2-carbonyl chloride (84 mg, 0.54 mmol) in the presence of DIEA (137 μL, 0.79 mmol) to afford 52.7 mg (47%) of the title compound as a light yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 9.65 (s, 1H), 8.50 (d, 1H, J=8.8 Hz), 7.92 (s, 1H), 7.71 (s, 1H), 7.37 (dd, 1H, J=2.5, 8.8 Hz), 7.29 (d, 1H, J=3.8 Hz), 7.23 (d, 1H, J=3.7 Hz), 6.46-6.45 (m, 1H), 2.94-2.89 (m, 4H), 2.14 (s, 3H), 1.85-1.80 (m, 4H), 1.66 (br s, 2H); Mass spectrum (ESI, m/z): Calcd. for C21H21N5O2, 376.1 (M+H), found 376.1.

Provenance & Evidence