Diisopropylethylamine → 4-Chloro-1-({5-[3-methyl-5-(trifluoromethyl)-4-isoxazolyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-1H-indole-5-carbonitrile

Participants

Reaction Steps

Synthesized as described in Example 32A and Example 33 using (1Z)-2-(4-chloro-5-cyano-2-propyl-1H-indol-1-yl)-N-hydroxyethanimidamide (0.030 g, 0.1 mmol) in anhydrous THF (5 mL) with propanephosphonic acid cyclic anhydride (T3P) (0.034 g, 0.12 mmol), 3-methyl-5-(trifluoromethyl)-4-isoxazolecarboxylic acid (0.0195 g, 0.1 mmol) and DIEA (0.016 mg, 0.12 mmol) and stirred at rt for 1 h and then heated at 120° C. for 2 h in the microwave: 1H NMR (400 MHz, CDCl3-d) δ 7.89 (s, 1 H), 7.52 (d, J=8.4 Hz, 1 H), 7.46 (d, J=8.4 Hz, 1 H), 5.47 (s, 2 H), 2.97 (t, 2 H), 2.55 (s, 3 H), 1.79-1.70 (m, 2 H), 1.05 (t, 3 H); MS (ES) m/z 450 (M+1).

Provenance & Evidence