Reaktion #57959

Reaktionsgleichung

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

biphenyl-4-carbaldehyde oxime

cesium carbonate

→

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

Ausbeute 68.2%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis compound was produced
2. 2
   SonstigeThe crude material was purified by flash chromatography through silica gel

Vorschrift

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), biphenyl-4-carbaldehyde oxime (0.14 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 4-[3-({[(1E)-1,1′-biphenyl-4-ylmethylidene]amino}oxy)propoxy]-2-{[3,5-bis(trifluoromethyl)benzoyl]amino}benzoic acid methyl ester (0.29 g, 68%) as a white solid. 1H NMR (500 MHz, DMSO-d6); δ 11.79 (s, 1H), 8.52 (s, 2H), 8.43 (s, 1H), 8.31 (s, 1H), 8.11 (d, 1H), 7.98 (d, 1H), 7.97-7.64 (AA′BB′, 4H), 7.45 (t, 2H), 7.37 (t, 1H), 6.89 (dd, 1H), 4.31 (t, 2H), 4.23 (t, 2H), 3.84 (s, 3H), 2.18 (m, 2H).

Quelle