1-Benzyl 3-ethyl 4-fluoroisophthalate → 1-Benzyl 3-ethyl 4-(3-(butyl(3,4-dichlorobenzyl)carbamoyl)-4-chloro-5-methyl-1H-pyrazol-1-yl)isophthalate

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Intermediate 1E, 1-benzyl 3-ethyl 4-fluoroisophthalate (Intermediate 91B, 270 mg, 0.89 mmol) and N-butyl-4-chloro-N-(3,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxamide (Intermediate 179B, 502 mg, 1.34 mmol) were converted to the title compound (458 g, 78%). 1H NMR (CDCl3, mixture of amide rotamers) δ 8.68 (dd, J=19.3, 1.9 Hz, 1H), 8.33 (dt, J=7.9, 2.0 Hz, 1H), 7.54-7.34 (m, 8H), 7.24-7.07 (m, 1H), 5.43 (d, J=3.1 Hz, 2H), 4.79-4.63 (m, 2H), 4.19 (q, J=7.3 Hz, 1H), 3.94 (q, J=7.2 Hz, 1H), 3.48-3.33 (m, 2H), 2.16 (d, J=6.6 Hz, 3H), 1.68-1.46 (m, 2H), 1.41-1.31 (m, 1H), 1.25-1.14 (m, 2.5H), 1.09 (t, J=7.2 Hz, 1.5H), 0.96-0.88 (m, 1.5H), 0.79 (t, J=7.4 Hz, 1.5H); MS(ESI+) m/z 656.0 (M+H)+.

Provenance & Evidence