Reaction #57961

Reaction equation

2-(3,5-bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester

4-trifluoromethyl-benzaldehyde oxime

cesium carbonate

→

2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-{3-[({(1E)-[4-(trifluoromethyl)phenyl]methylidene}amino)oxy]propoxy}benzoic acid methyl ester

Yield 78.6%

Solvents

acetone

Conditions

Workup

1. 1
   OtherThis compound was produced
2. 2
   OtherThe crude material was purified by flash chromatography through silica gel

Procedure

This compound was produced using similar methods as those used in Step 5, example 27, starting with 2-(3,5-bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester (0.35 g, 0.66 mmol), 4-trifluoromethyl-benzaldehyde oxime (0.13 g, 0.70 mmol) and cesium carbonate (0.86 g, 2.65 mmol) in acetone (25 mL). The crude material was purified by flash chromatography through silica gel using diethyl ether/hexanes (0/100 gradient to 10/90) to give 2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-{3-[({(1E)-[4-(trifluoromethyl)phenyl]methylidene}amino)oxy]propoxy}benzoic acid methyl ester (0.33 g, 78%) as a white solid. 1H NMR (500 MHz, DMSO-d6); δ 11.78 (s, 1H), 8.51 (s, 2H), 8.45 (s, 1H), 8.37 (s, 1H), 8.10 (d, 1H), 7.97 (d, 1H), 7.79-7.71 (AA′BB′, 4H), 6.88 (dd, 1H), 4.34 (t, 2H), 4.22 (t, 2H), 3.85 (s, 3H), 2.18 (m, 2H).

Source