4-(Difluoromethoxy)aniline → 1-[(6-Aminopyridin-3-yl)methyl]-3-{[4-(difluoromethoxy)phenyl]amino}-4-phenyl-1H-pyrrole-2,5-dione

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Reaction Conditions

Reaction Steps

A mixture of tert-butyl {5-[(3-chloro-2,5-dioxo-4-phenyl-2,5-dihydro-1H-pyrrol-1-yl)methyl]pyridin-2-yl}carbamate ( 0.70 g, 1.7 mmol) and 4-(difluoromethoxy)-aniline (0.54 g, 3.4 mmol) in DMF (4 mL) was heated in a microwave reactor at 150° C. for eight min. The solvent was evaporated and the residue was purified on a column (Isolute® SI, 10 g/70 mL), using CH2Cl2 and then CH3OH/CH2Cl2 (1:99, 2:98 and then 5:95) as eluant, to give 0.4 g (54%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.99 (bs, 1H), 7.67-7.62 (m, 2H), 7.14-7.04 (m, 3H), 6.91 (d, J=8 Hz, 2H), 6.78 (d, J=8 Hz, 1H), 6.72 (d, J=9 Hz, 2H), 6.63 (d, J=9 Hz, 2H), 6.33 (t, J=74 Hz, 1H), 4.60 (s, 2H).

Provenance & Evidence